Trifluoroacetic acid → [4-(5-Bromo-2-fluoro-benzyl)-phenylethynyl]-triisopropyl-silane

HRID 502087Notes

Reaction equation

HRID 502087 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:12][CH:11]=2)O)[CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([CH:7]=1)[CH2:8][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:23])[CH3:24])[CH:19]([CH3:20])[CH3:21])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57809581(5-Bromo-2-fluoro-phenyl)-{4-[(triisopropylsilyl)-ethynyl]-phenyl}methanol

Product 1

HCID 16065645[4-(5-Bromo-2-fluoro-benzyl)-phenylethynyl]-triisopropyl-silane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.6 g (5-bromo-2-fluoro-phenyl)-{4-[(triisopropylsilyl)-ethynyl]-phenyl}methanol and 4.1 ml triethylsilane in 50 ml dichloromethane is cooled in an ice bath. Then 4.7 ml trifluoroacetic acid are slowly added dropwise, and the solution is stirred for 4 h at ambient temperature. The solution is diluted with dichloromethane and washed with aqueous sodium hydrogen carbonate solution. After drying over sodium sulfate the solvent is removed and the residue is purified using silica gel (cyclohexane).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate solution
  2. dry with materialAfter drying over sodium sulfate the solvent
  3. customis removed
  4. customthe residue is purified

Sources & evidence

ORD record
ord-fb657bb8a2d84b589804409eb0c78f31
Source dataset
uspto-grants-2010_08
Patent number
US07772378B2

Reaction notes

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