Carbon tetrabromide → N-methanesulfonyl-6-bromomethylindole

HRID 1106776Notes

Reaction equation

HRID 1106776 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14]O)[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][Br:36])[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18789614N-methanesulfonyl-6-hydroxymethylindole

Product 1

HCID 18789641N-methanesulfonyl-6-bromomethylindoleYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of N-methanesulfonyl-6-hydroxymethylindole (340 mg, 1.51 mmol, from above) and triphenylphosphine (Ph3P) (415 mg, 1.58 mmol) in 5 ml of dry CH2Cl2 was cooled to 0° C. and a solution of carbon tetrabromide (551 mg, 1.66 mmol) in 3 ml dry CH2Cl2 was added dropwise via cannula (2 ml CH2Cl2 rinse). The reaction mixture was allowed to warm to room temperature. After 4 hr, the solvent was removed by rotary evaporation and the resultant purple oil was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane) to give 290 mg of N-methanesulfonyl-6-bromomethylindole, a colorless oil which solidified on standing (67% yield).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customthe resultant purple oil was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-036b273268c3419f9a0763292081e137
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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