Hydrochloric Acid → 4-Amino-2-bromo-5-fluorobenzoic acid

HRID 1807773ノート

反応式

HRID 1807773 の反応式
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([Br:13])[CH:3]=1.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Br:13])[CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67059665HCID 67059665、化合物

生成物 1

HCID 670596864-Amino-2-bromo-5-fluorobenzoic acid収率 89.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of the intermediate methyl 4-amino-2-bromo-5-fluorobenzoate (5.24 mmol, 1.3 g) in tetrahydrofuran (15 mL) was treated with a solution of lithium hydroxide (15.72 mmol, 0.66 g) in water (15 mL) and stirred at 60° C. for 4 hours. The reaction mixture was then cooled to room temperature, taken to ˜pH 5 with dilute hydrochloric acid and concentrated under vacuum. The residue was dissolved in tetrahydrofuran and purified by column chromatography (9:1 dichloromethane/methanol) to give the title compound (1.1 g). 1H NMR ((CD3)2SO, 400 MHz): δ6.11 (2H, s), 7.02 (1H, d), 7.52 (1H, d)

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in tetrahydrofuran
  4. custompurified by column chromatography (9:1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-5e1d0713d8ae4bf797455065963261ca
出典データセット
uspto-grants-2013_01
特許番号
US08357679B2

反応ノート

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