Bromotrimethylsilane → HCID 14626581, compound

HRID 359956Notes

Reaction equation

HRID 359956 reaction equation
[CH3:1][Si:2](Br)([CH3:4])[CH3:3].[F:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:8]=1[NH2:9]>C1C=CC=CC=1>[CH3:1][Si:2]([CH3:4])([CH3:3])[NH:9][C:8]1[C:7]([F:6])=[CH:13][CH:12]=[CH:11][C:10]=1[F:14]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 796472,6-Difluoroaniline

Product 1

HCID 14626581HCID 14626581, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Trimethylsilyl bromide, 10.24 ml (77.5 mmole), was added to 6 ml (55.7 mmole) of 2,6-difluoroaniline in 70 ml of benzene. There was a slight exotherm and immediate precipitation. Triethylamine, 10.8 ml (77.5 mmole), was added and the mixture stirred at room temperature for 16 hours. The mixture was filtered and the solvent removed from the filtrate in vacuo. The product was purified as described in Example 1 to provide 8.85 g (51.1 mmole, 91.7 percent yield) of 99.3 percent pure N-trimethylsilyl-2,6-difluoroaniline as a colorless liquid, b.p. 89°-91° C. at 18 mm.

Workup

  1. customa slight exotherm and immediate precipitation
  2. additionTriethylamine, 10.8 ml (77.5 mmole), was added
  3. filtrationThe mixture was filtered
  4. customthe solvent removed from the filtrate in vacuo
  5. customThe product was purified

Sources & evidence

ORD record
ord-aea22da04f1a42bf901f39e5fea855bb
Source dataset
uspto-grants-1991_03
Patent number
US05003096

Reaction notes

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