2-Bromobenzaldehyde → 1-(2-Bromophenyl)prop-2-en-1-ol

HRID 1484995Notes

Reaction equation

HRID 1484995 reaction equation
[CH2:1]([Mg]Br)[CH:2]=C.[Br:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]>C1COCC1>[Br:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]([OH:10])[CH:1]=[CH2:2]

Participants

4

Reactant 2

HCID 811292-BromobenzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 191022201-(2-Bromophenyl)prop-2-en-1-olYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of allylmagnesium bromide (108 mL, 108 mmol, 2.0 eq) in THF was added a solution of 2-bromobenzaldehyde (10 g, 54 mmol, 1.0 eq) in THF (20 mL) dropwise at −18° C. The mixture was allowed to reach room temperature for 17 h, then, quenched with saturated NH4Cl aqueous. The mixture was partitioned between brine and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to provide 1-(2-bromophenyl)prop-2-en-1-ol (10.5 g, 91%). LC-MS (m/z)=213.0 [M+H]+.

Workup

  1. customquenched with saturated NH4Cl aqueous
  2. customThe mixture was partitioned between brine and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-21114ca439ff42f0ae7bd97e98d99433
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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