Dimethylformamide → 3'-Fluoro[1,1'-biphenyl]-3-carboxylic acid

Temperature

100 °C

To a solution of (3-fluorophenyl)boronic acid (790 mg, 3.57 mmol, 1.0 eq), 3-bromobenzoic acid (790 mg, 3.93 mmol, 1.1 eq) and Na2CO3 (142 mg, 1.03 mmol, 2.5 eq) in a mixture of EtOH (2.5 mL), DMF (10 mL) and H2O (2.5 mL) was added Pd(PPh3)4 (170 mg, 0.18 mmol, 0.05 eq). The mixture was stirred at 100° C. overnight. Water was added and the aqueous layer was extracted with EtOAc and the organic extract was discarded. The aqueous layer was acidified to pH 4-5 with 1M HCl and extracted with EtOAc. The combined organic extracts were filtered through silica gel and evaporated in vacuo to give the title compound as a white solid (440 mg, 56%).

1. extractionthe aqueous layer was extracted with EtOAc
2. extractionthe organic extract
3. extractionextracted with EtOAc
4. filtrationThe combined organic extracts were filtered through silica gel
5. customevaporated in vacuo

ORD record

ord-30e8993d5cd946e8a829fabfc2fe9760

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249085B2