Selective ortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes
Emmanuelle Dubost; Christine Fossey; Thomas Cailly; Sylvain Rault; Frederic Fabis; Journal of Organic Chemistry 76 (2011) 6414–6420; doi:10.1021/jo200853j

data_4026485
_publ_section_title
;
 Selective ortho-Bromination of Substituted Benzaldoximes Using
 Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted
 2-Bromobenzaldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6414
_journal_page_last               6420
_journal_paper_doi               10.1021/jo200853j
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        synthetised
_chemical_formula_moiety         'C8 H7 Br N2 O3'
_chemical_formula_sum            'C8 H7 Br N2 O3'
_chemical_formula_weight         259.07
_chemical_melting_point          391
_chemical_name_systematic
;
2-bromo-5-nitrobenzaldehyde O-methyloxime
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.8740(2)
_cell_length_b                   15.5103(4)
_cell_length_c                   17.3312(5)
_cell_measurement_reflns_used    9049
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      39.75
_cell_measurement_theta_min      2.88
_cell_volume                     1847.81(9)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'BRUKER SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            68498
_diffrn_reflns_theta_full        40.26
_diffrn_reflns_theta_max         40.26
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.430
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_correction_T_min  0.4245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 software'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_description       prisme
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         5779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.9895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                4404
_reflns_number_total             5779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200853j_si_001.cif
_cod_data_source_block           ed20j
_cod_database_code               4026485