Triphenylmethyl phosphonium bromide → HCID 57961535, compound

Temperature

20 °C

A solution of triphenylmethylphosphonium bromide (28.4 g, 79.5 mmol) in tetrahydrofuran (152 mL) at 0° C. was treated with 2.5 M n-butyllithium in hexanes (31.8 mL, 79.5 mmol) dropwise and stirred at 0° C. for 15 min and at 20° C. for 1 h. The reaction mixture was cooled to 0° C., treated with a solution of tert-butyl (3-bromo-5-formylphenyl)carbamate (10.9 g, 36.2 mmol) in tetrahydrofuran (55 mL), and stirred at 20° C. for 1 h. The reaction mixture was cooled to 0° C., quenched with water (50 mL), concentrated to remove most of the tetrahydrofuran, poured into water (150 mL), and extracted with ethyl acetate (200 mL). The aqueous layer was separated and extracted with additional ethyl acetate (100 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude tan oil. This material was purified by flash column chromatography to give the desired product (9.9 g, 92%) as a white solid. LCMS for C9H9BrNO2 ([M-(t-Bu)+H]+H)+: m/z=241.9, 243.8.

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringstirred at 20° C. for 1 h
3. temperatureThe reaction mixture was cooled to 0° C.
4. customquenched with water (50 mL)
5. concentrationconcentrated
6. customto remove most of the tetrahydrofuran
7. additionpoured into water (150 mL)
8. extractionextracted with ethyl acetate (200 mL)
9. customThe aqueous layer was separated
10. extractionextracted with additional ethyl acetate (100 mL)
11. washThe combined organic extracts were washed with brine (100 mL)
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationfiltered
14. customevaporated

ORD record

ord-8997ae5fe2684393920d059450f58527

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2