Carbon tetrabromide → HCID 18695961, compound

HRID 1870611Notes

Reaction equation

HRID 1870611 reaction equation
[O:1]=[S:2]1(=[O:21])[C:6]2[CH:7]=[CH:8][C:9]3[O:14][CH2:13][CH2:12][O:11][C:10]=3[C:5]=2[C:4](=[O:15])[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19]O.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[O:1]=[S:2]1(=[O:21])[C:6]2[CH:7]=[CH:8][C:9]3[O:14][CH2:13][CH2:12][O:11][C:10]=3[C:5]=2[C:4](=[O:15])[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][Br:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18695960HCID 18695960, compound

Product 1

HCID 18695961HCID 18695961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dioxido-2-(4-hydroxybutyl)-4,5-ethylenedioxy-1,2-benzisothiazol-3(2H)-one (313 mg, 1 mmol) and carbon tetrabromide (432 mg, 1.3 mmol) in methylene chloride (2 mL) cooled in an ice bath under a nitrogen atomosphere was added dropwise a solution of triphenylphosphine (341 mg, 1.3 mmol) in methylene chloride (3.5 mL). The reaction was allowed to stir with gradual warming to room temp. over a four hour period and then the solvent was evaporated and the residue chromatographed on a column of silica gel by elution with chloroform to give crystalline 1,1-dioxido-2-(4-bromobutyl)-4,5-ethylenedioxy-1,2-benzisothiazol-3(2H)-one from diethyl ether/hexane, melting point 135-136° C.

Workup

  1. temperaturewith gradual warming to room temp. over a four hour period
  2. customthe solvent was evaporated
  3. customthe residue chromatographed on a column of silica gel by elution with chloroform

Sources & evidence

ORD record
ord-0f88116f74ce451881997ac756d2b33d
Source dataset
uspto-grants-2000_08
Patent number
US06096763

Reaction notes

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