4-Bromobenzaldehyde → HCID 60798668, compound

HRID 1501071Notes

Reaction equation

HRID 1501071 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([Mg]Br)[CH:11]([CH3:13])[CH3:12]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178418816HCID 178418816, compound

Product 1

HCID 60798668HCID 60798668, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzaldehyde (2 g, 10.8 mmol) in tetrahydrofuran (30 mL) in a two-necked round flask was cooled to −5° C. under nitrogen atmosphere. After 0.5 hour, isobutylmagnesium bromide (8 mL) was added dropwise. And then the mixture was warmed to room temperature. The resultant reaction mixture was quenched with saturated ammonium chloride aqueous solution (10 mL) and extracted with ethyl acetate (10 mL×3). The organic layers were combined, dried over sodium sulfate and concentrated to give a residue. The crude product was purified by silica gel column chromatography (silica gel, petroleum ether/ethyl acetate=8:1) to give 1-(4-bromophenyl)-3-methylbutan-1-ol (0.35 g, 13%). 1H NMR (300 MHz, CDCl3): δ 7.48-7.45 (m, 2H), 7.25-7.21 (m, 2H), 4.74-4.72 (m, 1H), 1.72-1.68 (m, 2H), 1.47-1.46 (m, 1H), 0.95 (d, J=6.0 Hz, 6H).

Workup

  1. customThe resultant reaction mixture
  2. customwas quenched with saturated ammonium chloride aqueous solution (10 mL)
  3. extractionextracted with ethyl acetate (10 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe crude product was purified by silica gel column chromatography (silica gel, petroleum ether/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-630b9483553f4776904bdb70b5576881
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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