Boron tribromide → HCID 178444415, compound

HRID 1090601Notes

Reaction equation

HRID 1090601 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 2N 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 2N 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-4a1cc68f65bf4ae2b8b6d24935c12a7d
Source dataset
uspto-grants-1992_01
Patent number
US05082589

Reaction notes

Loading…