2-(2-Bromophenyl)acetaldehyde → 1-(2-Bromophenyl)-2-pentanol

HRID 1771444Notes

Reaction equation

HRID 1771444 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][CH3:13]>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][CH2:12][CH3:13]

Participants

4

Reactant 2

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

Product 1

HCID 607992791-(2-Bromophenyl)-2-pentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-bromophenyl)acetaldehyde (16 g, 80.8 mmol) in THF (100 ml) was added propyl magnesium bromide (48 ml (2.0 M) in THF), 97 mmol) at 0° C. then stirred at room temperature for 5 h. The reaction mixture was quenched with ammonium chloride then the title compound was purified by separation methods A, E and H. (Yield 740 mg). The enantiomer-2 showed up at tr=5.70 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 ammonium chloride
  2. customthe title compound was purified by separation methods A, E and H
  3. customshowed up at tr=5.70 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-1c4e0901344445729aa012584840f55d
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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