Methanol → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanol

HRID 511000Notes

Reaction equation

HRID 511000 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].CO.[BH4-].[Na+]>O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:10]([OH:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866669121-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone

Product 1

HCID 866669131-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone (3.8 g, 14 mmol) in methanol (30 mL, 800 mmol) was added sodium tetrahydroborate (0.83 g, 22 mmol) at 0° C. The mix was stirred at 0° C. for 1 hour. Water (10 mL) was added to the mixture. The mixture was concentrated to about 30 mL. The residue was diluted with EtOAc, washed with water and brine, dried over magnesium sulfate and evaporated to yield the desired compound (3.9 g, 100%). LCMS calculated for C9H8BrClFO (M−OH)+: m/z=264.9, 266.9. found: 265.0, 267.0.

Workup

  1. concentrationThe mixture was concentrated to about 30 mL
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9eeb5845f8bc49b49310b0e2e758b34b
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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