Benzoyl chloride → HCID 80073716, compound

HRID 1486837Notes

Reaction equation

HRID 1486837 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1.[NH4+].[Cl-]>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[Br:14][C:15]1[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[C:20]=1[C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:12].[Br:14][C:15]1[CH:16]=[C:17]([O:23][CH3:24])[C:18]([C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:12])=[C:19]([O:21][CH3:22])[CH:20]=1

Participants

9

Reactant 4

HCID 7412Benzoyl chlorideHCID 25517Ammonium ChlorideHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 2

HCID 80073716HCID 80073716, compoundHCID 90013819HCID 90013819, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a cooled suspension of AlCl3 (150 mg, 1.2 eq) in 2 mL of anhydrous DCM at 0° C., was added dropwise benzoyl chloride (120 μL, 1.1 eq). Once the mixture was become limpid (15 min), 1-bromo-3,5-dimethoxybenzene (208 mg, 0.958 mmol) solubilized in 1 mL of DCM was slowly added at 0° C. After 1 h15 of stirring at low temperature, the yellow reaction mixture was hydrolyzed with a saturated NH4Cl solution (6 mL) The aqueous layer, more diluted with water and with a saturated NaHCO3 solution, was extracted with DCM (3×12 mL) The combined extracts were washed with aq. NaHCO3 solution (20 mL), with brine (20 mL), dried over MgSO4 and solvents were removed in vacuo. The crude was purified by silica gel flash chromatography (cyclohexane/AcOEt 100:0 to 93:7) and allowed to isolate (2-bromo-4,6-dimethoxyphenyl)(phenyl)methanone (264 mg) and (4-bromo-2,6-dimethoxyphenyl)(phenyl)methanone (29.4 mg) in 95% chemical yield (90/10 ratio) as white solids. 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=8.5 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.79 (s, 2H), 3.70 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 194.4 (C═O), 158.1 (C), 137.4 (C), 133.6 (CH), 129.5 (2CH), 128.6 (2CH), 124.2 (C), 116.9 (C), 108.0 (2CH), 56.3 (2OCH3); MS (ESI) m/z: 321.0, 322.9 [M+H, 79Br, 81Br]+; 243.1, 244.9 [M-Ph, 79Br, 81Br]+.

Workup

  1. additionwas slowly added at 0° C
  2. extractionwas extracted with DCM (3×12 mL) The combined extracts
  3. washwere washed with aq. NaHCO3 solution (20 mL), with brine (20 mL)
  4. dry with materialdried over MgSO4 and solvents
  5. customwere removed in vacuo
  6. customThe crude was purified by silica gel flash chromatography (cyclohexane/AcOEt 100:0 to 93:7)

Sources & evidence

ORD record
ord-72814091c98f479c9cac766df3e8aa88
Source dataset
uspto-grants-2016_08
Patent number
US09428500B2

Reaction notes

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