Tetrahydrofuran → HCID 69674030, compound

Temperature

70 °C

A flask containing 267 mg of tetrakis(triphenylphosphine)palladium and 1.00 g of 2,4-dibromothiazole was subjected to nitrogen substitution. To this flask, 9 ml of dry tetrahydrofuran and 9.9 ml of a 0.5 M benzylzinc bromide tetrahydrofuran solution were added. The obtained mixture was stirred at 70° C. for 6 hours. Thereafter, the reaction solution was cooled to a room temperature, and 30 ml of water was then added thereto, followed by extraction with 30 ml of ethyl acetate twice. The organic layer was washed with 30 ml of water twice and then with 30 ml of a saturated brine once. The resultant was dried over magnesium sulfate. The magnesium sulfate was filtrated, and the organic layer was then concentrated. The residue was then purified by column chromatography (Wako Gel C-200; hexane:ethyl acetate=14:1), so as to obtain 0.36 g of 2-benzyl-4-bromothiazole.

1. temperatureThereafter, the reaction solution was cooled to a room temperature
2. extractionfollowed by extraction with 30 ml of ethyl acetate twice
3. washThe organic layer was washed with 30 ml of water twice
4. dry with materialThe resultant was dried over magnesium sulfate
5. filtrationThe magnesium sulfate was filtrated
6. concentrationthe organic layer was then concentrated
7. customThe residue was then purified by column chromatography (Wako Gel C-200; hexane:ethyl acetate=14:1)

ORD record

ord-8fba7ea780434b059312a73a8e7e44b7

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586505B2