Methanol → Methyl 4-Bromo-2-chlorobenzoate

Temperature

0 °C

4-Bromo-2-chlorobenzoic acid (COMBI-BLOCK; CA-4187; 1 000 mg; 4.25 mmol; 1 eq.) was dissolved in MeOH (20 mL). The resulting solution was cooled down to 0° C. and thionyl chloride (1.23 mL; 16.99 mmol; 4 eq.) was added dropwise. After addition, the reaction mixture was stirred at RT. As the reaction was complete, solvents were evaporated. The crude mixture was dissolved in EtOAc and washed with NaHCO3 sat. and NaCl sat. solutions. The organic phase was dried over MgSO4, filtrated and evaporated to give the title compound (871 mg, 82%). 1H NMR (CDCl3, 300 MHz) δ 7.72 (d, J=8.3 Hz, 1H), 7.64 (d, J=1.9 Hz, 1H), 7.46 (dd, J=8.5, 1.9 Hz, 1H), 3.93 (s, 3H). HPLC (Method A) Rt 4.22 min (Purity: 98.5%).

1. additionAfter addition
2. customsolvents were evaporated
3. dissolutionThe crude mixture was dissolved in EtOAc
4. washwashed with NaHCO3 sat. and NaCl sat. solutions
5. dry with materialThe organic phase was dried over MgSO4
6. filtrationfiltrated
7. customevaporated

ORD record

ord-2abb643ab73d49208e4c0936d5fcfa3f

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202865B2