Sodium borohydride → 3-Bromo-2-(hydroxymethyl)phenol

HRID 1473913

反応式

HRID 1473913 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 119547682-Bromo-6-hydroxybenzaldehyde

生成物 1

HCID 861260253-Bromo-2-(hydroxymethyl)phenol収率 60%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-bromo-6-hydroxybenzaldehyde (3.8 g, 18.91 mmol, 1 eq.) in a mixture of THF and MeOH (4/1, 25 mL) was added NaBH4 (1.4 g, 37.81 mmol, 1.5 eq.) at rt portion-wise. Upon the completion of addition, the mixture was continued to stir at rt for 30 min. The mixture was quenched with HCl (4 N) and extracted with EtOAC twice. The combined organic layer was dried over Na2SO4, concentrated, and purified on silica gel using 25% EtOAc/hexanes as eluent to give 3-bromo-2-(hydroxymethyl)phenol (2.3 g, 60%) as a colorless oil.

後処理

  1. additionUpon the completion of addition
  2. customThe mixture was quenched with HCl (4 N)
  3. extractionextracted with EtOAC twice
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel using 25% EtOAc/hexanes as eluent

出典と根拠

ORDレコード
ord-b6a2b4f73fb24d26b0093fbe1e9f338d
出典データセット
uspto-grants-2015_04
特許番号
US09018210B2

関連ノート

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