Sodium borohydride → 2-(2-Fluoro-4-nitrophenyl)ethan-1-ol

HRID 1842954ノート

反応式

HRID 1842954 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12](OC)=[O:13].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 18369150Methyl 2-Fluoro-4-nitrophenylacetate

生成物 1

HCID 866721582-(2-Fluoro-4-nitrophenyl)ethan-1-ol収率 77.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of methyl 2-(2-fluoro-4-nitrophenyl)acetate (3.0 g, 14.0 mmol, 1.0 eq) in methanol (30 mL) was added NaBH4 (2.08 g, 36.3 mmol, 4.0 eg) at 0° C. and stirred at 70° C. for 16 h, then the methanol was evaporated and the residue was diluted with water (30 mL), the pH adjusted to being neutral with 2N HCl and the mixture extracted with EtOAc (50 mL×3). The organic layer was separated, washed with brine, dried over Na2SO4 and the solvent evaporated to yield 2-(2-fluoro-4-nitrophenyl)ethanol (2.0 g, 77%) as a viscous oil (TLC system: EtOAc/PE (3:7), Rf: 0.3).

後処理

  1. customthe methanol was evaporated
  2. additionthe residue was diluted with water (30 mL)
  3. extractionthe mixture extracted with EtOAc (50 mL×3)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-2fe3bc86216640c5a2587b8ddce146db
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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