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

HRID 1501051Notes

Reaction equation

HRID 1501051 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1>O1CCCC1>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([OH:12])[CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 217141961-(4-Bromophenyl)-2-methylpropan-1-olYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of isopropylmagnesium chloride (17.0 L, 1M in tetrahydrofuran) was added dropwise to the solution of 4-bromobenzaldehyde (2.1 g, 11.4 mol) in tetrahydrofuran (30 mL) at −10° C. Then the mixture was stirred at 25° C. for 4 hours. The resultant reaction was quenched with saturated ammonium chloride aqueous (20 mL). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 1-(4-bromophenyl)-2-methylpropan-1-ol (620 mg, 24%). 1H NMR (300 MHz, CDCl3): δ 7.98-7.85 (m, 2H), 7.48-7.35 (m, 2H), 5.17 (s, 1H), 4.49 (d, J=6.6 Hz, 1H), 2.35-2.30 (m, 1H), 1.01 (d, J=6.6 Hz, 6H).

Workup

  1. customThe resultant reaction
  2. customwas quenched with saturated ammonium chloride aqueous (20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1488824b04884e2d85276deb0c66aa61
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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