Water → 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1501082Notes

Reaction equation

HRID 1501082 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+].O>C(O)C>[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 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 101050696-Bromo-1-tetralone

Product 1

HCID 184699326-Bromo-1,2,3,4-tetrahydronaphthalen-1-olYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-bromo-3,4-dihydronaphthalen-1(2H)-one (1.0 g, 4.4 mmol) in ethanol (10 mL) was added sodium borohydride (0.8 g, 21 mmol). The reaction mixture was stirred at room temperature for 0.5 hour. After the reaction, the mixture was poured into water (100 mL) and the mixture was extracted with dichloromethane (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the pure product 6-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (1.0 g, 100%).

Workup

  1. customAfter the reaction
  2. extractionthe mixture was extracted with dichloromethane (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c227d258eb5141fca3423dc62b1df341
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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