Sodium borohydride → 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 63632

Reaction equation

HRID 63632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[BH4-].[Na+]>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 101050696-Bromo-1-tetralone

Product 1

HCID 184699326-Bromo-1,2,3,4-tetrahydronaphthalen-1-olYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8692e0a624043d49fcbd98aacc92b89
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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