1-(2-Bromophenyl)propan-2-one → HCID 89604109, compound

HRID 1771445Notes

Reaction equation

HRID 1771445 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:11])[CH3:10].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C@H:9]([OH:11])[CH3:10]

Participants

4

Reactant 2

HCID 27340921-(2-Bromophenyl)propan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 89604109HCID 89604109, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-bromophenyl) propane-2-one (30 g, 140 mmol) in MeOH (100 ml) was added NaBH4 (6.09 g, 210 mmol) at 0° C. and stirred at room temperature for 2 h. The reaction mixture was quenched with water and concentrated under reduced pressure to afford crude compound. The title compound was purified by separation methods A, E and M (Yield 28.0 g). The enantiomer-1 showed up at tr=7.86 min with Chiralcel OD-H (4.6×250 mm) 5μ, hexane:2-PrOH:TFA (90:5:0.1), 1 ml/min.

Workup

  1. customThe reaction mixture was quenched with water
  2. concentrationconcentrated under reduced pressure
  3. customto afford crude compound
  4. customThe title compound was purified by separation methods A, E and M (Yield 28.0 g)
  5. customshowed up at tr=7.86 min with Chiralcel OD-H (4.6×250 mm) 5μ, hexane:2-PrOH:TFA (90:5:0.1), 1 ml/min.

Sources & evidence

ORD record
ord-2b0ea41c76014a7489c1f98b4c7deae2
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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