Boron tribromide → 1-(3-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

HRID 2180590Notes

Reaction equation

HRID 2180590 reaction equation
C[O:2][C:3]1[C:4]([C:15](=[O:17])[CH3:16])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:4]([C:15](=[O:17])[CH3:16])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22490902HCID 22490902, compound

Product 1

HCID 224907981-(3-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-86, 14.2 g, 61.2 mmol) in dichloromethane (350 mL) at −78° C. was added boron tribromide (1 M in hexane, 80 mL, 80 mmol). After stirring from −78° C. to room temperature over 3 h the reaction mixture was quenched with sodium bicarbonate at −10° C. and extracted with diethyl ether. Combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from diethyl ether afforded the title compound as a brown solid.

Workup

  1. customwas quenched with sodium bicarbonate at −10° C.
  2. extractionextracted with diethyl ether
  3. washwere washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-b1d7a48745d846c882e20f113e39778b
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…