Thionyl Chloride → 5-[(3-Chloro-2-fluorophenyl)methyl]-2,4-dimethoxybenzoyl chloride

HRID 391236Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][C:6]1[C:7]([O:17][CH3:18])=[CH:8][C:9]([O:15][CH3:16])=[C:10]([CH:14]=1)[C:11](O)=[O:12].S(Cl)([Cl:25])=O>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][C:6]1[C:7]([O:17][CH3:18])=[CH:8][C:9]([O:15][CH3:16])=[C:10]([CH:14]=1)[C:11]([Cl:25])=[O:12]

Participants

Conditions

Temperature: 75 °C

Procedure

Under a nitrogen atmosphere, 5-(3-chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid (4.7 g) was dissolved in DMF/toluene solution (25 mL) (DMF concentration: 300 ppm). Thionyl chloride (2.1 g) was added dropwise to this solution at 75° C. After stirring at 75° C. for 1 hr, completion of the reaction was confirmed by HPLC. Toluene and excess thionyl chloride were evaporated under reduced pressure. Toluene (20 mL) was added to the concentrated residue, and the mixture was concentrated again under reduced pressure to give 5-(3-chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid chloride (5.07 g). THF (15 mL) was added thereto to give a suspension of acid chloride (5-(3-chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid chloride) in THF, which was directly used in the next step.

Workup

customToluene and excess thionyl chloride were evaporated under reduced pressure
additionToluene (20 mL) was added to the concentrated residue
concentrationthe mixture was concentrated again under reduced pressure

Sources & evidence

ORD record: ord-3cad465d98c744959c1726417ec82f9e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383819B2

Reaction notes

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