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ChemicalBook CAS DataBase List 2,3-DIHYDRO-1-BENZOFURAN-7-SULFONYL CHLORIDE

2,3-DIHYDRO-1-BENZOFURAN-7-SULFONYL CHLORIDE synthesis

3synthesis methods
-

Yield:953408-82-7 94%

Reaction Conditions:

in 1,2-dichloro-ethane;

Steps:

1 Preparation of 7-chlorosulfonyl-2,3-dihydrobenzo[b]furan (2)

Example 1 Preparation of 7-chlorosulfonyl-2,3-dihydrobenzo[b]furan (2) 2,3-Dihydrobenzo[b]furan (1) (Aldrich, 5.6 mL, 50 mmol) was added to a suspension of sulfur trioxide-dimethylformamide complex (Aldrich, 9.2 g, 60 mmol) in 1,2-dichloroethane (Aldrich, 20 mL). After being heated at 80° C. for 1 hour, the reaction mixture was cooled to room temperature, and thionyl chloride (Aldrich, 4.5 mL, 57 mmol) was introduced. The reaction mixture was then heated at 70° C. for 3 hours. After cooling down to room temperature, the reaction mixture was poured into ice water (100 mL) which was extracted with ether (3*30 mL). Combined organic layers were washed with brine, then dried (MgSO4). Removal of solvent under vacuum yielded a light yellow solid (10.2 g, 94%). TLC Rf 0.45 (9:1 of hexane-ethyl acetate); MS (electrospray) 219 (M+1); 1H NMR (CDCl3) δ3.35 (t, 2H, J=7.2 Hz), 4.78 (t, 2H, J=7.2 Hz), 6.92 (d, 1H, J=3.1 Hz), 7.82 (s, 1H), 7.83 (d, 1H, J=3.1 Hz).

References:

US6541467,2003,B1

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