Sodium borohydride → 4-Bromo-2-fluoro-5-(hydroxymethyl)phenol

HRID 1020787ノート

反応式

HRID 1020787 の反応式
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:6][C:7]([OH:11])=[C:8]([F:10])[CH:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 866364542-Bromo-4-fluoro-5-hydroxybenzaldehyde

生成物 1

HCID 667264354-Bromo-2-fluoro-5-(hydroxymethyl)phenol収率 99.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2-bromo-4-fluoro-5-hydroxybenzaldehyde (2.0 g, 9.1 mmol) in MeOH (15 mL) was cooled in an ice bath before treatment of NaBH4 (390 mg, 10.3 mmol). After the complete addition of NaBH4, the reaction mixture was allowed to stir for 1 h at room temperature before it was quenched with equal volume of water. EtOAc (20 mL) was added to the reaction solution and the layers were separated. The aqueous layer was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 4-bromo-2-fluoro-5-(hydroxymethyl)phenol (2.0 g, 83%).

後処理

  1. customwas quenched with equal volume of water
  2. additionEtOAc (20 mL) was added to the reaction solution
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with equal volume of EtOAc before the organic layers
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-77c7c4b6a21f455097083c1d5dda53e7
出典データセット
uspto-grants-2014_05
特許番号
US08716478B2

反応ノート

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