Hydrochloric Acid → (6-Bromobenzo[d]isothiazol-3-yl)(4-chlorophenyl)methanone

HRID 340151Notes

Reaction equation

HRID 340151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:25]=[CH:24][C:14]2[C:15]([C:18](N(OC)C)=[O:19])=[N:16][S:17][C:13]=2[CH:12]=1.Cl>C1COCC1>[Br:10][C:11]1[CH:25]=[CH:24][C:14]2[C:15]([C:18]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:19])=[N:16][S:17][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866583536-bromo-N-methoxy-N-methylbenzo[d]isothiazole-3-carboxamideHCID 178478191HCID 178478191, compound

Product 1

HCID 67436732(6-Bromobenzo[d]isothiazol-3-yl)(4-chlorophenyl)methanoneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorophenyl magnesium bromide (1.0N in THF, 16 mL, 16 mmol) was added to a stirred solution of 6-bromo-N-methoxy-N-methylbenzo[d]isothiazole-3-carboxamide (3.5 g, 12 mmol) in THF (100 mL). The reaction mixture was stirred at 0° C. for 1 hour. The reaction was poured into 1N HCl and extracted into ether. The combined organic layers were washed with brine, dried and concentrated. The crude product was suspended in ether and stirred for 15 minutes. The solid was collected by filtration to give (6-bromobenzo[d]isothiazol-3-yl)(4-chlorophenyl)methanone (3.3 g, 81%). 1H NMR (CDCl3, 400 MHz) δ □8.60 (d, J=8.8 Hz, 1H), 8.23 (d, J=8.4 Hz, 2H), 8.19 (s, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H).

Workup

  1. extractionextracted into ether
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. stirringstirred for 15 minutes
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-d6432ed1591b47ea825967e17ad2e068
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

Loading…