Sodium Carbonate → 4-Bromo-2-methoxybenzoyl chloride

HRID 432256Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:21])=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:21])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

Reactant 3

HCID 10340Sodium Carbonate

HCID 24386Thionyl Chloride

HCID 134507554-Bromo-2-methoxybenzoic acid

Product 1

HCID 223467824-Bromo-2-methoxybenzoyl chlorideYield 100%

Conditions

Temperature: 80 °C

Procedure

4-Bromo-2-methoxybenzoic acid (2.934 g, 12.70 mmol) was mixed with sodium carbonate (2.2 g, 26.51 mmol). Thionyl chloride (20 mL) was added and the reaction mixture was heated at 80° C. for 16 hours. After distilling off excess thionyl chloride, heptane was added and the solid was collected by filtration to give 4-bromo-2-methoxy-1-benzenecarbonyl chloride (3.16 g, 100%). 1H NMR (CDCl3) δ 3.94 (s, 3H), 7.16 (s, 1H), 7.20 (d, J=8.51 Hz, 1H), 7.95 (d, J=8.51 Hz, 1H).

Workup

distillationAfter distilling off excess thionyl chloride, heptane
additionwas added
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-24fdaf023ac14a24b0d3ab337925aec1
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660744B1

Reaction notes

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