Boron tribromide → HCID 178418577, compound

HRID 5307Notes

Reaction equation

HRID 5307 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178418593HCID 178418593, compound

Product 1

HCID 178418577HCID 178418577, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 7.5 g trans-4-(2-[4-methoxyphenyl]ethyl)cyclohexanol and 100 ml of dichloromethane was treated at 0° C. with 27 ml of a 1M solution of boron tribromide in dichloromethane. The reaction mixture was stirred at room temperature for a further 2 hours and then poured on to 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 water, sodium hydrogen carbonate solution and again with water and then dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from hexane and gave 5.2 g of trans-4-(2-[4-hydroxyphenyl]ethyl)cyclohexanol.

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 water, sodium hydrogen carbonate solution and again with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-93d2d1036cf4487bb97588f4d5c4c71e
Source dataset
uspto-grants-1993_09
Patent number
US05244597

Reaction notes

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