4-Bromobenzaldehyde → 1-(4-Bromophenyl)-2-methylpropan-1-ol

HRID 650037Notes

Reaction equation

HRID 650037 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH:10]([CH3:12])[CH3:11])[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 178418918HCID 178418918, compound

Product 1

HCID 217141961-(4-Bromophenyl)-2-methylpropan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 9.0 g (0.048 mol) of 4-Bromobenzaldehyde in 150 mL of ether at 0° C. under argon, 2.0 M solution of isopropyl magnesium chloride in ether (29.2 mL) was added and stirred for 30 minutes. The solution was slowly warmed up to room temperature and stirred for an additional 4 hours. The mixture was then added to 150 mL of aqueous saturated sodium bicarbonate and extracted with 200 mL of ether. The organic extract was washed once with water, dried and evaporated to afford 9.8 g (95%) of the product as a gum.

Workup

  1. stirringstirred for an additional 4 hours
  2. extractionextracted with 200 mL of ether
  3. extractionThe organic extract
  4. washwas washed once with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-56854620dda542ea81ea32866449a1b8
Source dataset
uspto-grants-2001_08
Patent number
US06271248B1

Reaction notes

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