Hydrochloric Acid → 2,3-Dihydro-1,4-benzodithiin-6-carbaldehyde

To 5 mL of a tetrahydrofuran solution containing 500 mg of 6-bromo-2,3-dihydro-1,4-benzodithiin, 0.67 mL of a 2.67 mol/L butyllithium/hexane was added at −78° C., the mixture was stirred for 0.5 hour, then 300 mg of ethyl formate was added thereto, and the mixture was further stirred for 2 hours. Thereto was added 1 mol/L hydrochloric acid, and ethyl acetate was then added to the mixture. The organic layer was separated, washed with an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane 1:4] to obtain 121 mg of a brown oily substance, 2,3-dihydro-1,4-benzodithiin-6-carbaldehyde.

1. additionwas added at −78° C.
2. stirringthe mixture was further stirred for 2 hours
3. additionwas then added to the mixture
4. customThe organic layer was separated
5. washwashed with an aqueous saturated sodium hydrogen carbonate solution
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was removed under reduced pressure
8. customThe residue thus obtained
9. customwas purified by silica gel column chromatography [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane 1:4]

ORD record

ord-5cbaf46ad22a48cfa9423265367ab23d

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329694B2