Hydrochloric Acid → 1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

HRID 1404577Notes

Reaction equation

HRID 1404577 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[C:12](=[O:14])[CH3:13].Cl>CO>[Cl:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[CH:12]([OH:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27339821-(2,6-Dichloro-3-fluorophenyl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 12 ml of methanol at 0° C. was added 1.55 g (41.1 mmol, 1.7 eq) of NaBH4, followed by a solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone (5.0 g, 24.1 mmol, 1.0 eq) in 10 ml of methanol. The reaction was warmed to room temperature (r.t.) and stirred for 2 hours. A 1.0M HCl solution was added, and the solution was extracted with dichloromethane (DCM), dried, and evaporated to a white solid, 5.6 g, in 111% crude yield. The product was used for next reaction without further purification.

Workup

  1. extractionthe solution was extracted with dichloromethane (DCM)
  2. customdried
  3. customevaporated to a white solid, 5.6 g, in 111% crude yield
  4. customThe product was used for next reaction without further purification

Sources & evidence

ORD record
ord-54b972615d65444f938d5a4c4110d6d7
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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