Methanol → Methyl 2-(2-bromophenyl)acetate

Temperature

0 °C

In a 250 mL round bottom flask, 5.0046 g (23.2729 mmol, 1.0 eq) of 2-(Bromophenyl)acetic acid was dissolved in 100 mL of clean, dry MeOH under N2 atmosphere. This solution was cooled to 0° C. using a wet ice bath and stirred for five minutes. To the stirring solution was added 2.55 mL (34.9093 mmol, 1.5 eq) of thionyl chloride dropwise over a period of five minutes. The reaction was then allowed to stir overnight, gradually warming to room temperature. The following morning, the solvent was removed under reduced pressure. The resultant deep yellow oil was taken up in 50 mL of DCM. The solution was then washed with 50 mL of saturated NaHCO3 (aq) solution. The organic layer immediately became colorless. The layers were separated and the organic layer was washed with brine (1×30 mL) and then dried over Na2SO4. The solution was decanted and then solvent was removed under reduced pressure. A clear oil was isolated. LCMS (m/e): 230 (M+H); 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.69 (s, 3H) 3.82 (s, 2H) 7.10-7.25 (m, 1H) 7.26-7.40 (m, 2H) 7.58 (d, J=7.91 Hz, 1H).

1. stirringto stir overnight
2. temperaturegradually warming to room temperature
3. customThe following morning, the solvent was removed under reduced pressure
4. washThe solution was then washed with 50 mL of saturated NaHCO3 (aq) solution
5. customThe layers were separated
6. washthe organic layer was washed with brine (1×30 mL)
7. dry with materialdried over Na2SO4
8. customThe solution was decanted
9. customsolvent was removed under reduced pressure
10. customA clear oil was isolated

ORD record

ord-37412275ce114a9b98387eac5ee2105a

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623911B2