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

HRID 2192455Notes

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

Conditions

Temperature: 0 °C

Procedure

4-Chlorophenyl magnesium bromide (1.0 N 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

extractionextracted into ether
washThe combined organic layers were washed with brine
customdried
concentrationconcentrated
stirringstirred for 15 minutes
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-bcd691ac1393422a89a9c66eaac039d6
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329709B2

Reaction notes

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