tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 57545200, compound

HRID 1661524Notes

Reaction equation

HRID 1661524 reaction equation
[Br:1][CH:2]1[C:6](=[O:7])[C:5]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][Cl:15])=[CH:11][C:4]=2[O:3]1.FC(F)(F)S(O[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[O:3][C:4]2[CH:11]=[C:10]([O:12][CH2:13][CH2:14][Cl:15])[CH:9]=[CH:8][C:5]=2[C:6]=1[O:7][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 57545177HCID 57545177, compound

Product 1

HCID 57545200HCID 57545200, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

1.50 g (5.15 mmol) of the hydrate of 2-bromo-6-(2-chloroethoxy)benzofuran-3-one (Example 43A) are concentrated three times with toluene under argon in order to remove water azeotropically. The residue is then dissolved under argon in 25 ml of diethyl ether and cooled to 0° C. 0.79 ml (5.66 mmol) of TEA and 1.30 ml (5.66 mmol) of tert-butyldimethylsilyl trifluoromethanesulfonate are successively slowly added dropwise, and the mixture is stirred at 0° C. for 10 min and at RT for 1 h. The diethyl ether phase is then separated off, the residue is extracted twice with diethyl ether, and the combined diethyl ether phases are concentrated. Column chromatography on silica gel 60 (mobile phase: cyclohexane) results in 2.00 g (96% of theory) of the product.

Workup

  1. customto remove water azeotropically
  2. dissolutionThe residue is then dissolved under argon in 25 ml of diethyl ether
  3. customThe diethyl ether phase is then separated off
  4. extractionthe residue is extracted twice with diethyl ether
  5. concentrationthe combined diethyl ether phases are concentrated
  6. customColumn chromatography on silica gel 60 (mobile phase: cyclohexane) results in 2.00 g (96% of theory) of the product

Sources & evidence

ORD record
ord-37369a0ac257461483ad98afe1ef7add
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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