Bromine → HCID 69316420, compound

HRID 2115154Notes

Reaction equation

HRID 2115154 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Br:23]Br>C(Cl)Cl.ClC1C=CC=CC=1>[Br:23][C:18]1[CH:17]=[C:16]([CH:13]2[CH2:14][CH2:15][CH:10]([CH:7]3[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)[CH2:11][CH2:12]2)[CH:21]=[CH:20][C:19]=1[OH:22]

Participants

5

Reactant 2

HCID 24408BromineHCID 3107829Phenol, 4-(4'-propyl[1,1'-bicyclohexyl]-4-yl)-

Product 1

HCID 69316420HCID 69316420, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 7964ChlorobenzeneSolvent

Procedure

4-(4-(4-Propylcyclohexyl)cyclohexyl)phenol (0.5 g) was dissolved in a mixed solvent of methylene chloride (5 ml) and chlorobenzene (1 ml), to which was then added dropwise a solution of bromine (0.28 g) in methylene chloride (2 ml) under ice cooling while stirring. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes, added in ice water, and then extracted with methylene chloride. An organic layer was washed with water, rinsed with a sodium thiosulfate aqueous solution, and then dried over anhydrous magnesium sulfate. The methylene chloride solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a white crystal (0.25 g) of 2-bromo-4-(4-(4-propylcyclohexyl)cyclohexyl)phenol.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. extractionextracted with methylene chloride
  4. washAn organic layer was washed with water
  5. washrinsed with a sodium thiosulfate aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe methylene chloride solution was concentrated in vacuo
  8. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-b94c86d56e814276b1f8b237f4271a31
Source dataset
uspto-grants-2008_10
Patent number
US07435455B2

Reaction notes

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