2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-5-nitro-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione

HRID 840196Notes

Reaction equation

C([O-])(O)=O.[Na+].[N+:6]([C:9]1[CH:10]=[CH:11][C:12]2[NH:16][S:15](=[O:18])(=[O:17])[CH2:14][C:13]=2[CH:19]=1)([O-:8])=[O:7].Br[CH2:21][CH2:22][F:23]>O>[F:23][CH2:22][CH2:21][N:16]1[C:12]2[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:19][C:13]=2[CH2:14][S:15]1(=[O:18])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

NaHCO3 (0.93 g, 11.0 mmol) is dissolved in H2O (15 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (1.90 g, 8.9 mmol) is added with stirring. The mixture is heated to 80° C. for 0.5 hrs and a yellow solid formed. The mixture is cooled to 0° C. and filtered. The solid is washed with cold H2O (15 mL) then with cold EtOH (25 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (15 mL). 1-Bromo-2-fluoroethane (1.52 mL, 20.0 mmol) is added and the solution heated to 100° C. for 4 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (1.55 g, 67%) after recrystallization from EtOH. Mp 142-4° C. HRMS (FAB) calcd for C9H9FN2O4S +NA1 283.0165, found 283.0166.

Workup

customa yellow solid formed
temperatureThe mixture is cooled to 0° C.
filtrationfiltered
washThe solid is washed with cold H2O (15 mL)
customThe yellow solid thus obtained
customis dried under high vacuum
dissolutionthen dissolved in dry DMF (15 mL)
temperaturethe solution heated to 100° C. for 4 hrs
temperatureThe solution is cooled to room temperature
filtrationThe solid is collected by filtration

Sources & evidence

ORD record: ord-694c4096000c4d0cbab2205b160e4118
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365612B2

Reaction notes

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