Bromine → HCID 178444414, compound

HRID 1762021Notes

Reaction equation

HRID 1762021 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:21]Br>ClCCl>[Br:21][C:18]1[CH:19]=[C:14]([CH2:13][CH2:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)[CH:15]=[CH:16][C:17]=1[OH:20]

Participants

4

Reactant 2

HCID 24408BromineHCID 178444415HCID 178444415, compound

Product 1

HCID 178444414HCID 178444414, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.7 g of 4-[2-(trans-4-pentylcyclohexyl)ethyl]phenol in absolute dichloromethane was treated dropwise at 0° C. with a solution of 1.6 g of bromine in 20 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 3.4 g of 2-bromo-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenol.

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-7bda133d8e234d8aa3113bbc7994b53e
Source dataset
uspto-grants-1989_05
Patent number
US04830470

Reaction notes

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