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

HRID 594782Notes

Reaction equation

HRID 594782 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-bc968291c54242589df24b4ec0aba449
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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