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

HRID 521392Notes

Reaction equation

HRID 521392 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-b7c331785f334371a5bac24e9813e6be
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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