Water → (4-Bromophenyl)(4-chlorophenyl)methanol

HRID 924732Notes

Reaction equation

HRID 924732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.O>O1CCCC1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[OH:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 707414-BromobenzaldehydeHCID 178478191HCID 178478191, compound

Product 1

HCID 57659206(4-Bromophenyl)(4-chlorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorophenylmagnesium bromide (12.97 ml, 1M solution in diethyl ether) was added slowly to a solution of 4-bromobenzaldehyde (2.0 g, 10.81 mmol) in tetrahydrofuran (25 ml) at 0° C., under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and was stirred for 17 hours. Water (3 ml) was then added and the solvent was removed under reduced pressure. The residue was then partitioned between ethyl acetate and 1N HCl solution. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was then purified by column chromatography (SiO2), eluting with ethyl acetate/petroleum ether (1:9), to yield the title compound (2.30 g). LC/MS: (PS-B3) Rt 3.49 [M−H]+ 297.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was then partitioned between ethyl acetate and 1N HCl solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was then purified by column chromatography (SiO2)
  8. washeluting with ethyl acetate/petroleum ether (1:9)

Sources & evidence

ORD record
ord-e7c413f1475744d2b44928497e882aee
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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