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

HRID 391236ノート

反応式

HRID 391236 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21735183Dimethylformamide toluene溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cad465d98c744959c1726417ec82f9e
出典データセット
uspto-grants-2013_02
特許番号
US08383819B2

反応ノート

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