Sodium borohydride → 1-(2-Bromophenyl)-4,4,4-trifluorobutan-2-ol

HRID 1771429Notes

Reaction equation

HRID 1771429 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[CH2:10][C:11]([F:14])([F:13])[F:12].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([OH:15])[CH2:10][C:11]([F:13])([F:14])[F:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 613929871-(2-Bromophenyl)-4,4,4-trifluorobutan-2-one

Product 1

HCID 613928691-(2-Bromophenyl)-4,4,4-trifluorobutan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-bromophenyl)-4,4,4-trifluorobutan-2-one (7.0 g, 24.9 mmol) in MeOH (150 ml) was added NaBH4 (1.23 g, 32.3 mmol) at 0° C. and stirred for 1 h at RT. Then the reaction mixture was quenched with MeOH and concentrated under reduced pressure to afford crude compound. The title compound was purified by separation methods A, E and H. (Yield 1.6 g of Enantiomer-1 and 1.4 g-Enantiomer-2). The enantiomer-1 showed up at tr=5.67 min and enantiomer-2 showed up at tr=9.57 min with Chiralcel OD-H (4.6×250 mm) 5μ, hexane:2-PrOH:TFA (90:10:0.1), 1 ml/min.

Workup

  1. customThen the reaction mixture was quenched with MeOH
  2. concentrationconcentrated under reduced pressure
  3. customto afford crude compound
  4. customThe title compound was purified by separation methods A, E and H
  5. customshowed up at tr=5.67 min and enantiomer-2
  6. customshowed up at tr=9.57 min with Chiralcel OD-H (4.6×250 mm) 5μ, hexane:2-PrOH:TFA (90:10:0.1), 1 ml/min.

Sources & evidence

ORD record
ord-c157767e795e4a0f8db0f0fb56749656
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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