Methyl iodide → Methyl 2-(4-bromophenyl)-2-methylpropanoate

To a stirred solution of compound 68b (5 g, 0.02 mol) in THF (100 mL) was added a 1 M THF solution of NaHMDS (22.6 mL, 22.6 mmol) at 0° C. under a nitrogen atmosphere. The resulting solution was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was then cooled to 0° C. and iodomethane (3.19 g, 22.5 mmol) was added dropwise. The ice-water bath was removed and stirring was continued for an additional hour at room temperature. The reaction mixture was then treated with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford compound 68c as brown oil. Mass Spectrum (GCMS, ESI pos.): Calcd. for C11H13BrO2: 256.0 (M). found: 256.0.

1. temperatureThe reaction mixture was then cooled to 0° C.
2. customThe ice-water bath was removed
3. stirringstirring
4. waitwas continued for an additional hour at room temperature
5. additionThe reaction mixture was then treated with water (50 mL)
6. extractionextracted with EtOAc (3×100 mL)
7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-a12629057336446c8ce8053f9053c7c4

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193736B2