Carbon tetrabromide → 4-Bromomethylbenzenesulfonamide

HRID 1162193Notes

Reaction equation

HRID 1162193 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C(Cl)Cl>[Br:33][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 100811624-(Hydroxymethyl)benzenesulfonamide

Product 1

HCID 131545004-BromomethylbenzenesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-hydroxymethyl-benzene-sulphonamide (0.105 mg, 0.56 mmoles) was dissolved in DCM (5 mL). Polymer supported triphenylphosphine (294 mg, 2.4 mmoles/g, 1.12 mmoles) was added, and the mixture was stirred with a shaker at room temperature for 10 minutes. CBr4 (557 mg, 1.68 mmoles) was then added, and stirring was continued for 3 hours. The supported reagent was removed by filtration, the solvent was evaporated, and the crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt 9/1) to yield the title compound as a light-yellow solid (70 mg).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 3 hours
  4. customThe supported reagent was removed by filtration
  5. customthe solvent was evaporated
  6. customthe crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt 9/1)

Sources & evidence

ORD record
ord-959b2cf596024fef80905e822d391f51
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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