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

HRID 1473913

반응식

HRID 1473913 반응식
[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

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 119547682-Bromo-6-hydroxybenzaldehyde

생성물 1

HCID 861260253-Bromo-2-(hydroxymethyl)phenol수율 60%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b6a2b4f73fb24d26b0093fbe1e9f338d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018210B2

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