Bromine → HCID 178444414, compound

HRID 1650583Notes

Reaction equation

HRID 1650583 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 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 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 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-e66a4aa2685648cdba2b9bb2ff150d7d
Source dataset
uspto-grants-1990_05
Patent number
US04925278

Reaction notes

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