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

HRID 1180411Notes

Reaction equation

HRID 1180411 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[CH:14]1([CH:20]=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[OH:21])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 16275CyclohexanecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 11402947(4-Bromophenyl)(cyclohexyl)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., cyclohexanecarboxaldehyde (42.4 mmol, 4.8 g) was added. The mixture was stirred at −78° C. for 0.5 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 0.5 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-af72c1d258794e4bbde62e380b7f6464
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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