Sodium borohydride → 2-(4-Bromo-2,6-dimethylphenyl)-2,2-difluoroethanol

HRID 708805Notes

Reaction equation

HRID 708805 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([F:16])([F:15])[C:10](OCC)=[O:11])=[C:4]([CH3:17])[CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>CCO.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([C:9]([F:15])([F:16])[CH2:10][OH:11])=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 118098676Ethyl 2-(4-bromo-2,6-dimethylphenyl)-2,2-difluoroacetate

Product 1

HCID 1180986772-(4-Bromo-2,6-dimethylphenyl)-2,2-difluoroethanolYield 100.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of Intermediate 7A (3.1 g, 10.09 mmol) in EtOH (30 ml) was added calcium chloride (0.336 g, 3.03 mmol). The resulting mixture was cooled to −10° C. and sodium borohydride (0.955 g, 25.2 mmol) was added. The mixture was then allowed to warm to rt and stand at rt. for 1 h. The reaction mixture was diluted with EtOAc and Sat. NaHCO3, extracted with EtOAc (×3). The combined organic layer was dried (MgSO4), concentrated to yield Intermediate 7B (2.68 g, 10.11 mmol, 100% yield) as a white solid. 19F NMR (376 MHz, methanol-d3) δ ppm −98.12 (br. s., 2F). 1H NMR (400 MHz, methanol-d3) δ ppm 2.42 (t, J=4.39 Hz, 6H) 3.92 (t, J=14.06 Hz, 2H) 7.26 (s, 2H).

Workup

  1. temperatureto warm to rt
  2. customstand at rt
  3. extractionextracted with EtOAc (×3)
  4. dry with materialThe combined organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd62a9d05fb248809545e75b039dd356
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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