Oxalyl chloride → HCID 18003808, compound

HRID 479084Notes

Reaction equation

HRID 479084 reaction equation
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[S:13])=[C:10]([CH3:17])[C:9]=1[O:18][CH3:19]>ClCCl>[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([Cl:4])=[S:13])=[C:10]([CH3:17])[C:9]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 178493644HCID 178493644, compound

Product 1

HCID 18003808HCID 18003808, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Difluoro-3-methoxybenzoic acid (38.2 g) was added to a stirred solution of methyl mercaptan (9.7 g) in dry tetrahydroftran under an inert atmosphere. A solution of n-butyl lithium (162 ml of a 2.5M solution in hexane) was added dropwise at −78° C. After 1 hour the mixture was allowed to warm to 20° C. overnight and evaporated. Hydrochloric acid (2M) and ether were added and the organic phase washed (water), dried mil (magnesium sulphate) and evaporated. The residue was triturated with hexane to give 4-fluoro-3-methoxy-2-methylthiobenzoic acid (29.2 g), NMR 2.6 (s, 3H), 4.0 (s, 3H), 7.1 (m, 1H), 7.9 (m, 1H). oxalyl chloride (51.5 g) was added to a stirred solution of 4-fluoro-3-methoxy-2-methylthiobenzoic acid (29.2 g) in dichloromethane. After 3.5 hours the mixture was evaporated to give the title compound (33.0 g), used directly in the above reactions.

Workup

  1. customAfter 3.5 hours the mixture was evaporated

Sources & evidence

ORD record
ord-445c33cc92124a7da7181bb158110255
Source dataset
uspto-grants-2003_11
Patent number
US06642418B1

Reaction notes

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