Boron tribromide → 4-[5-(4-Hydroxyphenyl)thiazol-2-yl]benzoic acid

HRID 2270052ノート

反応式

HRID 2270052 の反応式
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:9][CH:8]=1>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:11][CH:12]=1.[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:11][CH:12]=1

参加物

5

反応物 2

HCID 25134Boron tribromideHCID 18331084Methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate

生成物 2

HCID 183310804-[5-(4-Hydroxyphenyl)thiazol-2-yl]benzoic acid収率 211.3%HCID 18331082Methyl 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of boron tribromide (1.0M in dichloromethane, 97.7 ml) was added dropwise methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate (3.18 g) in dichloromethane (50 ml) at −78° C. The reaction mixture was allowed to warm to room temperature, and stirred for 2 hours. The reaction mixture was poured into ice-water (1000 ml), and stirred for 30 minutes at room temperature. The precipitate was collected by filtration, washed with water, and dried overnight to give in the proportion of 37:63 mixture of methyl 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoate and 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoic acid (3.07 g), and those were used without purification in the next reaction.

後処理

  1. stirringstirred for 30 minutes at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight

出典と根拠

ORDレコード
ord-8e353c564e2647b5802f8fa2ad8205c7
出典データセット
uspto-grants-2001_12
特許番号
US06331521B1

反応ノート

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