2-Chloro-4'-fluoroacetophenone → (R)-2-Chloro-1-(4-fluorophenyl)ethanol

HRID 1908240Notes

Reaction equation

HRID 1908240 reaction equation
B.C1COCC1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[Cl:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)=[O:31]>C1COCC1>[Cl:28][CH2:29][C@@H:30]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[OH:31]

Participants

5

Reactant 3

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 2723981Borane;tetrahydrofuranHCID 9838490(R)-2-Methyl-CBS-oxazaborolidine

Product 1

HCID 12300420(R)-2-Chloro-1-(4-fluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution consisting of BH3.THF (1 M, 150 mL) and (R)-(+)-2-methyl-CBS-oxazaborolidine (1 M in THF) (2.14 mL) was added a second solution consisting of 2-chloro-4′-fluoro-acetophenone (37.0 g, 214 mmol) and THF (100 ml) over 1 h at rt. The resultant colorless reaction mixture was stirred for 45 min and then quenched with MeOH (75 mL). The solvent was removed in vacuo leaving the title compound as pale yellow oil, which was used without further purification (37 g, 100%)

Workup

  1. additionwas added a second solution
  2. customquenched with MeOH (75 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2866d4f6b9e24bc28777598762ea65f6
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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