4-Bromobenzaldehyde → 1-(4-Bromophenyl)propan-1-ol

HRID 1501055Notes

Reaction equation

HRID 1501055 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1>O1CCCC1>[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]([OH:11])[CH2:1][CH3:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 1072901-(4-Bromophenyl)propan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (5.4 mL, 3 M solution in tetrahydrofuran) was added dropwise to the solution of 4-bromobenzaldehyde (2.0 g, 10.8 mmol) in tetrahydrofuran (30 mL) at −30° C. Then the resultant mixture stirred at room temperature for 4 hours. The reaction was quenched with saturated ammonium chloride aqueous. 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)propan-1-ol (2.0 g, 88%). 1H NMR (300 MHz, d6-DMSO): δ 7.49 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 5.20 (d, J=4.5 Hz, 1H), 4.45-4.41 (m, 1H), 1.63-1.53 (m, 2H), 0.80 (t, J=7.5 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-add373cdd3e84f7f96d4b427fe968e5d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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