2-(2-Bromophenyl)acetaldehyde → 1-(2-Bromophenyl)butan-2-ol

HRID 1771447Notes

Reaction equation

HRID 1771447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]=[O:10].[CH2:11]([Mg]Br)[CH2:12]C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([OH:10])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 114241802-(2-Bromophenyl)acetaldehydeHCID 178455851HCID 178455851, compound

Product 1

HCID 607991361-(2-Bromophenyl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-bromophenyl) acetaldehyde (15 g, 75.37 mmol) in THF (100 ml) was added propyl magnesium bromide (1.0 M in THF) (15.13 g, 113.6 mmol) at 0° C. then stirred at RT for 3 h. The reaction mixture was quenched with ammonium chloride then the title compound was purified by separation methods A, E and M. (Yield 7.0 g). The enantiomer showed up at tr=13.6 min with Chiralcel OJH (4.6×250 mm) 5μ, hexane:ethanol (98:02), 1 ml/min.

Workup

  1. customThe reaction mixture was quenched with ammonium chloride
  2. customthe title compound was purified by separation methods A, E and M
  3. customshowed up at tr=13.6 min with Chiralcel OJH (4.6×250 mm) 5μ, hexane:ethanol (98:02), 1 ml/min.

Sources & evidence

ORD record
ord-a05ba5b8246a46649122c434265a6137
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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