Boron tribromide → HCID 59627687、化合物

HRID 1930114ノート

反応式

HRID 1930114 の反応式
B(Br)(Br)Br.[Cl:5][C:6]1[C:7]([O:19]C)=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1>ClCCl>[Cl:5][C:6]1[C:7]([OH:19])=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 59627702HCID 59627702、化合物2 回

生成物 1

HCID 59627687HCID 59627687、化合物収率 72.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Boron tribromide (1.068 mL, 11.30 mmol) was added dropwise to ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-4; 456 mg, 1.88 mmol) in dichloromethane (10 mL) at ambient temperature under nitrogen. The resulting orange red solution was stirred at 0° C. for 45 minutes. The reaction mixture was carefully quenched with water (25 mL), extracted with EtOAc (2×100 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford crude product as a yellow gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-hydroxy-2-methylphenyl)acetate (310 mg, 72.2%) as a colourless oil which solidified on standing.

後処理

  1. customThe reaction mixture was carefully quenched with water (25 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product as a yellow gum
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-55e2275b12ac4ae59fe69811b0132e46
出典データセット
uspto-grants-2012_05
特許番号
US08188092B2

反応ノート

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