Boron tribromide → HCID 178444415, compound

HRID 1650580Notes

Reaction equation

HRID 1650580 reaction equation
B(Br)(Br)Br.[CH2:5]([C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)[CH2:6][CH2:7][CH2:8][CH3:9]>ClCCl>[CH2:5]([C@H:10]1[CH2:11][CH2:12][C@H:13]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[CH2:14][CH2:15]1)[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178444418HCID 178444418, compound

Product 1

HCID 178444415HCID 178444415, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.6 g of boron tribromide in 50 ml of absolute dichloromethane was treated dropwise at 0° C. with a solution of 2.0 g of 2-(trans-4-pentylcyclohexyl)-1-(4-methoxyphenyl)ethane in 50 ml of absolute dichloromethane. The mixture was stirred for 1 hour and then poured into ice-water. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed with 50 ml of 2 N sodium carbonate solution and several times with water, dried over magnesium sulphate and concentrated. Recrystallization of the resulting crude product from hexane at 0° C. gave 1.8 g of 4-[2-(trans-4-pentylcyclohexyl)ethyl]phenol of m.p. 102° C.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was back-extracted three times with 50 ml of dichloromethane each time
  3. washThe combined organic phases were washed with 50 ml of 2 N sodium carbonate solution and several times with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customRecrystallization of the resulting crude product from hexane at 0° C.

Sources & evidence

ORD record
ord-801356d033bd46cfbeddafe3f6c9f2bb
Source dataset
uspto-grants-1990_05
Patent number
US04925278

Reaction notes

Loading…