Triethylsilane → 5-Bromo-7-fluoro-1,1-dimethyl-indane

HRID 2202226Notes

Reaction equation

HRID 2202226 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH3:20])([CH3:19])[CH2:14][C:15]2=O)=[C:11]([F:21])[CH:10]=1>C(O)(C(F)(F)F)=O>[Br:8][C:9]1[CH:17]=[C:16]2[C:12](=[C:11]([F:21])[CH:10]=1)[C:13]([CH3:20])([CH3:19])[CH2:14][CH2:15]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 1186227516-Bromo-4-fluoro-3,3-dimethyl-indan-1-one

Product 1

HCID 1186227125-Bromo-7-fluoro-1,1-dimethyl-indane

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (1.59 g, 2.17 mL, 13.63 mmol) was added to a solution of 6-bromo-4-fluoro-3,3-dimethylindan-1-one (1.5 g, 5.83 mmol) in TFA (30 mL) at room temperature, and the mixture was stirred at room temperature for 40 hr. To the reaction mixture was added ice water at 0° C., and the mixture was extracted with ethyl acetate (×2). The organic layer was washed with aqueous sodium hydroxide solution (the pH of the aqueous layer was adjusted to 7.0) and 10% brine, dried over sodium sulfate, and concentrated under reduced pressure to give crude 5-bromo-7-fluoro-1,1-dimethylindane as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×2)
  2. washThe organic layer was washed with aqueous sodium hydroxide solution (the pH of the aqueous layer
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84cf30b851104db2996da042688435b0
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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