Hydrochloric Acid → 1-(4-Bromophenyl)-4-chlorobutan-1-ol

HRID 338525Notes

Reaction equation

HRID 338525 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 783174'-Bromo-4-chlorobutyrophenoneHCID 4311764Sodium borohydride

Product 1

HCID 146531501-(4-Bromophenyl)-4-chlorobutan-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-bromophenyl)-4-chlorobutan-1-one (1.00 g, 3.83 mmol) in methanol (20 mL) was added sodium borohydride (260 mg, 7.66 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour. 1M HCl was added and the mixture was stirred for 15 minutes. Solvents were removed and the residue was extracted with ethyl acetate (10 mL×2). The combined organic layer were washed with brine, dried and concentrated to give target compound (1 g, 99%) as a light yellow oil.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customSolvents were removed
  3. extractionthe residue was extracted with ethyl acetate (10 mL×2)
  4. washThe combined organic layer were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22f6c5449ba044039cf28353857ab528
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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