Carbon tetrabromide → HCID 17966545, compound

HRID 927055Notes

Reaction equation

HRID 927055 reaction equation
O[CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[S:7](=[O:11])(=[O:10])[CH2:8][CH2:9][C:5]=2[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[S:7](=[O:11])(=[O:10])[CH2:8][CH2:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17966965HCID 17966965, compound

Product 1

HCID 17966545HCID 17966545, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hydroxymethyl-2,3-dihydro-benzo[b]thiophene 1,1-dioxide (185 mg, 0.93 mmol) in CH2Cl2 (6 mL) was added triphenylphosphine (294 mg, 1.12 mmol) and carbon tetrabromide (371 mg, 1.12 mmol). After stirring for 14 h at rt, all volatiles were removed under reduced pressure. 5-Bromomethyl-2,3-dihydro-benzo[b]thiophene 1,1-dioxide (218 mg, 90%) was isolated by chromatography (33-50% ethyl acetate in hexanes).

Workup

  1. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-32e20032029249eaa96720c3bbbfedb0
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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