4'-Bromo-3-chloropropiophenone → 4-Bromo-alpha-(2-chloroethyl)benzenemethanol

HRID 2361801Notes

Reaction equation

HRID 2361801 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][Cl:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[CH2:9][CH2:10][Cl:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 957904'-Bromo-3-chloropropiophenoneHCID 4311764Sodium borohydride

Product 1

HCID 108006384-Bromo-alpha-(2-chloroethyl)benzenemethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-Bromo-phenyl)-3-chloro-propan-1-one (1 g, 4.04 mmol) in tetrahydrofuran (9 ml) and water (0.58 ml) was added sodium borohydride (0.16 g, 4.28 mmol). The reaction mixture was stirred at room temperature for 2 hours, quenched with careful addition of water and extracted with ethyl acetate. The organic layers were separated, dried (MgSO4), filtered and concentrated to afford the title compound, which was used in the next step without further purification. LC/MS: (PS-A2) Rt 3.07 [M+H]+ No Ionization.

Workup

  1. customquenched with careful addition of water
  2. extractionextracted with ethyl acetate
  3. customThe organic layers were separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f37cfd69214484caed9239bbad339a2
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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