Carbon Tetrachloride → 1,2-Benzisothiazole, 3-(bromomethyl)-6-fluoro-

HRID 10208Notes

Reaction equation

HRID 10208 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][S:8][C:4]=2[CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:38](Cl)(Cl)([Cl:40])[Cl:39]>>[CH2:38]([Cl:40])[Cl:39].[CH3:2][CH2:3][CH2:4][CH:5]([CH3:10])[CH3:6].[Br:12][CH2:9][C:6]1[C:5]2[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=2[S:8][N:7]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21978372HCID 21978372, compound

Product 2

HCID 219784071,2-Benzisothiazole, 3-(bromomethyl)-6-fluoro-Yield 51%HCID 86592985Dichloromethane isohexane

Procedure

A mixture of 6-fluoro-3-methyl-1,2-benzisothiazole [prepared by the method of D. M. Fink and J. T. Strupczewski, Tetrahedron Lett., 1993, 34, 6525] (761 mg, 4.55 mmol), N-bromosuccinimide (0.89 g, 5.0 mmol) and benzoyl peroxide (102 mg (70% (w/w)), 0.29 mmol) in CCl4 (25 mL) was heated at reflux under nitrogen for 6 h. The mixture was allowed to cool and filtered under suction. The filtrate was concentrated and the residue purified by flash silica chromatography, eluting with 1:2 then 1:1 DCM/isohexane to give the title compound as a white solid (569 mg, 51%). 1H NMR (500 MHz, CDCl3) δ 4.82 (3H, s), 7.25 (1H, dt, J=8.8 and 2.2 Hz), 7.60 (1H, dd, J=8.1 and 2.2 Hz), 8.07–8.10 (1H, m). (471 MHz, CDCl3)δF −111.9.

Workup

  1. customprepared by the method of D
  2. temperatureat reflux under nitrogen for 6 h
  3. temperatureto cool
  4. filtrationfiltered under suction
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by flash silica chromatography
  7. washeluting with 1:2

Sources & evidence

ORD record
ord-f875c6bfec5146bc8f103499ca380038
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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