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

HRID 2167141Notes

Reaction equation

HRID 2167141 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-6e3095ed84a448a09f9240a4b084a0ee
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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