Acetaldehyde → HCID 68408095, compound

Temperature

-78 °C

n-Butyl lithium (1.6M in hexane, 5.1 ml, 8.1 mmol) was added dropwise under nitrogen at −78° C. to a solution of (2-bromo-4-chloro-6-methoxy-3-methyl-phenyl)-carbamic acid tert-butyl ester (1.3 g, 3.7 mmol) in THF (22 ml). The reaction was stirred for 15 minutes at −78° C., and acetaldehyde (480 ul, 8.4 mmol) was added. The reaction was warmed overnight to r.t. Saturated aqueous ammonium chloride solution (10 ml) was added, the reaction was diluted with water and extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was treated with heptane and little methylene chloride. The title compound was filtered off as a yellow solid. The filtrate was purified by column chromatography (silica gel, heptane/ethyl acetate=1/1) to yield another batch of product, which gave a combined yield of 708 mg (79%).

1. temperatureThe reaction was warmed overnight to r.t
2. extractionextracted twice with diethyl ether
3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated
7. additionThe residue was treated with heptane and little methylene chloride
8. filtrationThe title compound was filtered off as a yellow solid
9. customThe filtrate was purified by column chromatography (silica gel, heptane/ethyl acetate=1/1)
10. customto yield another batch of product, which
11. customgave a combined yield of 708 mg (79%)

ORD record

ord-6802d40a4740478f816c34f01f3eaf2a

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790733B2