Regioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones
Leire Arias; Yosu Vara; Fernando P. Cossío; Journal of Organic Chemistry 77 (2012) 266–275; doi:10.1021/jo201841y

data_4026837
_publ_contact_author_address
;
Facultad de Qu\'imica, Dpto. Qu\'imica Org\'anica I;
Paseo manuel de Lardizabal 3, 20018 San Sebastian-Donostia, Spain;
;
_publ_contact_author_email       fp.cossio@ehu.es
_publ_contact_author_fax         '+34 943 01 5270'
_publ_contact_author_name        'Fernando P. Coss\'io'
_publ_contact_author_phone       '+34 943 01 5442'
_publ_section_title
;
 Regioselective Preparation of Benzo[b]furans from Phenols and
 \a-Bromoketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              266
_journal_page_last               275
_journal_paper_doi               10.1021/jo201841y
_journal_volume                  77
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.3
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_symmetry_space_group_name_Hall  '-P 1'
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_cell_angle_gamma                92.871(5)
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_cell_length_c                   11.9601(9)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    100(2)
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_cell_measurement_wavelength     0.71073
_cell_volume                     695.13(9)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
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_computing_molecular_graphics    'Diamond v.3.1f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
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_diffrn_ambient_temperature      100(2)
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_diffrn_measurement_details
;
  1 omega  -64.00   35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7080   77.0000 -150.0000 99

  2 omega   37.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7080   77.0000  150.0000 31

  3 omega  -53.00  -17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7080   77.0000  150.0000 36

  4 omega  -10.00  113.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1768   77.0000   60.0000 123

  5 omega    1.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1768   77.0000  -60.0000 123

;
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire2 (large Be window)'
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_diffrn_orient_matrix_UB_11      0.038767358
_diffrn_orient_matrix_UB_12      0.0831516585
_diffrn_orient_matrix_UB_13      0.0300301577
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_diffrn_orient_matrix_UB_22      -0.0042713533
_diffrn_orient_matrix_UB_23      0.0575497428
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_diffrn_orient_matrix_UB_32      -0.0203550017
_diffrn_orient_matrix_UB_33      0.0112231795
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5537
_diffrn_reflns_theta_full        28.3
_diffrn_reflns_theta_max         28.3
_diffrn_reflns_theta_min         3.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       'Cut prism'
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5134
_exptl_crystal_size_mid          0.2666
_exptl_crystal_size_min          0.2192
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2634
_reflns_number_total             3448
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201841y_si_001_2.cif
_cod_data_source_block           iksr81
_cod_database_code               4026837