Water → 1,4-Dihydro-2,3-benzoxathiin-3-oxide
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9]Br.O.O.OC[S:15]([O-:17])=[O:16].[Na+].O>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[CH2:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][S:15](=[O:16])[O:17]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 1,2-bis(bromomethyl)benzene (15 g, 56.8 mmol) in N,N-dimethylformamide (100 mL) at 0° C. was added tetrabutylammonium bromide (3.66 g, 11.4 mmol), followed by sodium hydroxymethane sulfinate dihydrate (17.5 g, 113.6 mmol) in one portion. The resulting suspension was stirred at 0° C. for 7 h under nitrogen and then at room temperature for 10 h. Water (250 mL) was added and after 30 min the reaction mixture was diluted with diethyl ether. The organic layer was washed with water twice. The aqueous layer was extracted with diethyl ether twice more. The combined organic layers were dried over anhydrous magnesium sulfate and evaporated under vacuum to yield the title compound (purity 80%). 13C NMR (400 MHz, CDCl3) δ 133.8, 130.0, 128.6, 127.9, 125.9, 125.7, 63.0, 57.0. 1H NMR (400 MHz, CDCl3) δ 7.20-7.41 (m, 4H), 5.31 (d, J=13.6 Hz, 1H), 4.97 (d, J=13.6 Hz, 1H), 4.42 (d, J=15.4 Hz, 1H), 3.56 (d, J=15.4 Hz, 1H). MS [M+H]+, 169.
Workup
- waitat room temperature for 10 h
- washThe organic layer was washed with water twice
- extractionThe aqueous layer was extracted with diethyl ether twice more
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-2be00d0cd626484a9d314353fe49a729
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365061B2
Reaction notes
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