1,4-Dibromobenzene → (4-Bromophenyl)(4-fluorophenyl)methanol

HRID 1180407Notes

Reaction equation

HRID 1180407 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:19]([C:18]2[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=2)[OH:20])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 680234-FluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 13354004(4-Bromophenyl)(4-fluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,4-dibromobenzene (42.4 mmol, 10 g) in THF (100 mL) at −78° C. was added dropwise n-BuLi (42.4 mmol, 2 M in hexane). The mixture was stirred at −78° C. for 0.5 h., 4-fluorobenzaldehyde (42.4 mmol, 5.3 g) was added. The mixture was stirred at −78° C. for 1 h and then warmed to r.t. The reaction mixture was diluted with EtOAc, washed with NaHCO3 and brine. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography gave the title compound.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 h
  2. temperaturewarmed to r.t
  3. washwashed with NaHCO3 and brine
  4. extractionThe organic extract
  5. dry with materialwas dried (anhyd. MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil

Sources & evidence

ORD record
ord-de1176094ff24a8fb1d54c199b4f521b
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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