Thionyl Chloride → 5-(3-Chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid chloride

HRID 391236노트

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HRID 391236 반응식
[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]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 248096205-(3-Chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid

생성물 1

HCID 248096955-(3-Chloro-2-fluorobenzyl)-2,4-dimethoxybenzoic acid chloride수율 102.1%

시약·촉매·용매 1

HCID 21735183Dimethylformamide toluene용매

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온도
75 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-3cad465d98c744959c1726417ec82f9e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383819B2

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