2-Bromobenzoyl chloride → 253309-48-7

Temperature

0 °C

To a solution of 2-bromobenzoyl chloride (1.3 mL, 9.9 mmol) in dry tetrahydrofuran (38 mL) at 0° C. under nitrogen was added dropwise a 2.0 M solution of isopropylmagnesium bromide in tetrahydrofuran (12.4 mL, 24.8 mmol) over ca. 5 minutes. The reaction mixture was stirred at 0° C. for 30 minutes then at room temperature for 27 hours. The reaction was quenched by the addition of 1 M aqueous hydrochloric acid (30 mL) and concentrated in vacuo to remove tetrahydrofuran. The aqueous phase was diluted to ca. 50 mL with water and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the crude product as an orange oil (2.1 g). Purification by flash chromatography using a solvent gradient of 1 to 4% ethyl acetate in hexane gave the title compound (0.77 g, 33%) as a clear, pale yellow oil.

1. waitat room temperature for 27 hours
2. customThe reaction was quenched by the addition of 1 M aqueous hydrochloric acid (30 mL)
3. concentrationconcentrated in vacuo
4. customto remove tetrahydrofuran
5. additionThe aqueous phase was diluted to ca. 50 mL with water
6. extractionextracted with ethyl acetate (2×50 mL)
7. washThe combined organic extracts were washed with water (50 mL) and brine (50 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give the crude product as an orange oil (2.1 g)
12. customPurification by flash chromatography

ORD record

ord-65a383901c4347a9a5f39ea7407c64c6

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678787B2