Hydrochloric Acid → 1-(2-Bromo-4-chlorophenyl)ethanol

HRID 405234

Reaction equation

HRID 405234 reaction equation
[BH4-].[Na+].C1COCC1.[Br:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16](=[O:18])[CH3:17].Cl>CO>[Br:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH:16]([OH:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 47126441-(2-Bromo-4-chlorophenyl)ethanone

Product 1

HCID 574450731-(2-Bromo-4-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid NaBH4 (354 mg, 9.4 mmol) was added to a 0° C., THF (5 mL) and MeOH (15 mL) solution of 1-(2-bromo-4-chlorophenyl)ethanone (1.8 g, 7.8 mmol). After 30 min 2N aqueous HCl was slowly added, and the resulting mixture was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-de0ade1835f8404786d55c3e197ec22f
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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