Reaction #710538

Reaction equation

methanesulfonyl chloride

4-bromobenzylalcohol

Et3N

→

methanesulfonic acid 4-bromo-benzyl ester

Yield 94.0%

Solvents

DCM

Conditions

Workup

1. 1
   Otherquenched with water
2. 2
   workup.ADDITIONSaturated aqueous NaHCO3 was added
3. 3
   Extractionthe product was extracted with DCM
4. 4
   Filtrationthe combined organic extracts were filtered through a phase separator cartridge
5. 5
   Concentrationconcentrated

Procedure

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, 2 H), 7.16 (d, 2 H), 4.05 (s, 2 H), 2.35 (s, 3 H).

Source