Triethylamine → HCID 11086667, compound

To a solution of 4-bromobenzylalcohol (2 g, 10.7 mmol) in DCM (30 mL) at 0° C. was added Et3N (2.2 mL, 16.0 mmol) followed by methanesulfonyl chloride (910 μL, 11.8 mmol). The reaction was allowed to warm to room temperature, stirred for 2 hours and then quenched with water. Saturated aqueous NaHCO3 was added, the product was extracted with DCM, the combined organic extracts were filtered through a phase separator cartridge and concentrated to give methanesulfonic acid 4-bromo-benzyl ester (2.67 g, 10 mmol, 94%). A solution of the crude product (2.67 g, 10 mmol) in DMSO (40 mL) was stirred at room temperature for 16 hours with potassium thioacetate (1.26 g, 11 mmol). The reaction was treated with water and extracted with DCM, filtered through a phase separator, concentrated and purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give thioacetic acid S-(4-bromo-benzyl)ester (1.81 g, 7.39 mmol, 69%). 1H NMR (300 MHz, CDCl3): δ 7.41 (d, 2H), 7.16 (d, 2H), 4.05 (s, 2H), 2.35 (s, 3H).

1. customquenched with water
2. additionSaturated aqueous NaHCO3 was added
3. extractionthe product was extracted with DCM
4. filtrationthe combined organic extracts were filtered through a phase separator cartridge
5. concentrationconcentrated

ORD record

ord-e48c52652e264b1c94e2c254c56bbb6a

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382222B2