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

HRID 2293665Notes

Reaction equation

HRID 2293665 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]Br)([CH3:12])[CH3:11]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 217141961-(4-Bromophenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a flame-dried flask under an argon atmosphere is added 1.85 g of commercially available 4-bromobenzaldehyde and charged with 30 mL of tetrahydrofuran. The solution is cooled to 0 ° C. and slowly treated with 7.0 mL of isopropylmagnesium bromide. After stirring overnight at room temperature the reaction mixture is concentrated under reduced pressure. The residue is partioned between diethyl ether and saturated ammonium chloride; the aqueous layer is then extracted with diethyl ether. The combined organic phases are dried (magnesium sulfate), and the volatiles are removed. The residue is flash column chromatographed using 30% to 60% diethyl ether in hexane to afford 1.25 g of the title product as a viscous, tan oil.

Workup

  1. concentrationis concentrated under reduced pressure
  2. extractionthe aqueous layer is then extracted with diethyl ether
  3. dry with materialThe combined organic phases are dried (magnesium sulfate)
  4. customthe volatiles are removed
  5. customchromatographed

Sources & evidence

ORD record
ord-065fd781e33f41478b82a05cd32cb4d7
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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