1,4-Dibromobutane → HCID 22313931, compound

HRID 347022Notes

Reaction equation

HRID 347022 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][O:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:9][S:10][C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 1358479523-(4-Bromo-phenyl)-benzo[d]isothiazol-6-ol

Product 1

HCID 22313931HCID 22313931, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

2.0 g (6.55 mmol) 3-(4-bromo-phenyl)-benzo[d]isothiazol-6-ol in 30 ml acetone were treated with 5.89 g (42.5 mmol, 6.5 eq) K2CO3 and 1.9 ml (16.33 mmol, 2.5 eq) 1,4-dibromobutane. The reaction mixture was stirred at 45° C. for 8 h and at RT over night, filtered and evaporated. The excess of dibromide was removed in vacuo and the crude product was purified by column chromatography on silica gel with a gradient EtOAc:hexane 1:9 to 1:4 to yield 2.0 g (71%) 6-(4-Bromo-butoxy)-3-(4-bromo-phenyl)-benzo[d]isothiazole as yellow semisolid, MS: 439 (M, 2Br).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe excess of dibromide was removed in vacuo
  4. customthe crude product was purified by column chromatography on silica gel with a gradient EtOAc:hexane 1:9 to 1:4

Sources & evidence

ORD record
ord-d5425586000e4798bd212456f6fe95a0
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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