Water → 2,2'-Isopropylidene bis(4-fluorophenol)

HRID 1413857Notes

Reaction equation

HRID 1413857 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:24])=[C:10]([C:12]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22]C)([CH3:14])[CH3:13])[CH:11]=1.O>ClCCl>[C:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[OH:22])([C:10]1[CH:11]=[C:6]([F:5])[CH:7]=[CH:8][C:9]=1[OH:24])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 202910912-(5-Fluoro-2-hydroxyphenyl)-2-(5-fluoro-2-methoxyphenyl)propane

Product 1

HCID 202910962,2'-Isopropylidene bis(4-fluorophenol)Yield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (1 ml) in dichloromethane (10 ml) was added dropwise to a solution of 2-(5-fluoro-2-hydroxyphenyl)-2-(5-fluoro-2-methoxyphenyl)propane (0.5 g) in dichloromethane (10 ml) at -70° C. The solution was stirred at this temperature for one hour and water was then added. The organic layer was separated, dried (Na2SO4) and the solvent removed to give a colourless product which crystallised from hexane to give colourless prisms of 2,2'-isopropylidene bis(4-fluorophenol) (0.375 g); m.p. 155° C.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. customthe solvent removed
  4. customto give a colourless product which
  5. customcrystallised from hexane

Sources & evidence

ORD record
ord-366d25fcf7204e49a1b8f5f73199c22d
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

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