Water → (3-Cyclopenten-1-yl) (4'-hydroxy-[1,1'-biphenyl]-4-yl)-methanone

HRID 65291Notes

Reaction equation

HRID 65291 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 20234281(3-Cyclopenten-1-yl)(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone

Product 1

HCID 54426410(3-Cyclopenten-1-yl) (4'-hydroxy-[1,1'-biphenyl]-4-yl)-methanoneYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3-cyclopenten-1-yl)(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone (42 g) in methylene dichloride (400 ml) was added over 1 h. to a solution of boron tribromide (30 ml) in methylene dichloride (200 ml) at -70° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm up slowly at room temperature and was stirred overnight. The solution was poured into water and the mixture was stirred for 10 min. The organic layer was washed twice with water, once with brine and dried (MgSO4). Removal of the solvent gave (3-cyclopenten-1-yl) (4'-hydroxy-[1,1'-biphenyl]-4-yl)-methanone (38.5 g). A small sample recrystallised from ethanol had m.p. 153°-155° C.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-df7b261e81d14d5a9a2b6e3bbe24ba7c
Source dataset
uspto-grants-1986_09
Patent number
US04613619

Reaction notes

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