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_4026836
_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. Cossio'
_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'
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_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2008)'
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_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
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'Superflip (Palatinus, 2008; van Smaalen, 2003)'
_diffrn_ambient_temperature      297(2)
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_diffrn_measurement_details
;
  1 omega  -59.00    7.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -21.7415   45.0000  300.0000    0.0000    0.0000 66

  2 omega -120.00   18.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -21.7415  -77.0000  150.0000    0.0000    0.0000 138

  3 omega  -15.00   51.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       22.2103   45.0000    0.0000    0.0000    0.0000 66

  4 omega  -68.00   -2.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       22.2103  -45.0000   90.0000    0.0000    0.0000 66

  5 omega   60.00  121.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       22.2103    0.0000   30.0000    0.0000    0.0000 61

  6 omega   -8.00   58.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       22.2103  -77.0000   30.0000    0.0000    0.0000 66

  7 omega   -6.00   47.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       22.2103  -77.0000    0.0000    0.0000    0.0000 53

;
_diffrn_measurement_device       '\k-geometry diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0743383757
_diffrn_orient_matrix_UB_12      -0.0016950673
_diffrn_orient_matrix_UB_13      0.0135438911
_diffrn_orient_matrix_UB_21      0.0037683163
_diffrn_orient_matrix_UB_22      0.0011930768
_diffrn_orient_matrix_UB_23      -0.0467601942
_diffrn_orient_matrix_UB_31      -0.0026754526
_diffrn_orient_matrix_UB_32      -0.0740615902
_diffrn_orient_matrix_UB_33      0.0155101053
_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
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11862
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction Ltd., 2008)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_description       'Cut prism'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.0070(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2559
_reflns_number_total             5547
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201841y_si_001_1.cif
_cod_data_source_block           dendrils35
_cod_original_cell_volume        1419.40(10)
_cod_database_code               4026836