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

HRID 2106414

Reaction equation

HRID 2106414 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 the 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 sulphate 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 sulphate the solvent
  3. customis removed
  4. customthe residue is purified

Sources & evidence

ORD record
ord-ab68764deff8446f9dc887ef2fccc268
Source dataset
uspto-grants-2009_08
Patent number
US07579449B2

Linked notes

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