Potassium borohydride → HCID 86685117, compound

HRID 1913000Notes

Reaction equation

HRID 1913000 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([F:19])[C:11]=2[F:20])=[O:9])[CH:7]=1.[BH4-].[K+]>Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([F:19])[C:11]=2[F:20])[OH:9])[CH:7]=1

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 86685116HCID 86685116, compound

Product 1

HCID 86685117HCID 86685117, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanone 3c (8.0 g, 21.3 mmol) was dissolved in 240 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of potassium borohydride (1.73 g, 32.0 mmol) in an ice bath. The reaction mixture was stirred for 16 hours at room temperature. Thereafter, 50 mL 1 M hydrochloric acid were added. The reaction mixture was concentrated under reduced pressure and extracted with dichloromethane (100 mL×2). The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanol 3d (8.0 g, yellow grease), which was used directly in the next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane (100 mL×2)
  3. extractionThe organic extract
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78511bc3fbdc4720a70ab414bc62934e
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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