Chlorotrimethylsilane → Methyl 2-(4-(bromomethyl)phenyl)acetate

To a stirred suspension of 2-(4-(bromomethyl)phenyl)acetic acid (5.00 g, 21.8 mmol, 1.0 eq.) in methanol (75 mL) was added chlorotrimethylsilane (0.64 mL, 5.02 mmol, 0.23 eq.) at room temperature. The resulting mixture was stirred at room temperature for 2 hr, at which time the reaction was a clear colorless solution. The volatile material was removed under reduced pressure, the residue dissolved in methanol (25 mL), and the volatile material was removed under reduced pressure. This process was repeated two additional times to afford methyl 2-(4-(bromomethyl)phenyl)acetate as an orange solid (5.30 g, quantitative yield). 1H NMR (CDCl3, 500 MHz) δ 7.37-7.33 (m, 2H), 7.26-7.24 (m, 2H), 4.48 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H). [Lit. J. Med. Chem. 2009, 52, 1180-9.]

1. customThe volatile material was removed under reduced pressure
2. dissolutionthe residue dissolved in methanol (25 mL)
3. customthe volatile material was removed under reduced pressure

ORD record

ord-27bd932e6e2c421493ab07ec9c6c7b08

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2