Potassium Carbonate → 2-Fluoro-5-(3-fluorophenyl)-3-methyl-benzoic acid

HRID 1771622Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:11][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 5-bromo-2-fluoro-3-methyl-benzoic acid (697 mg, 2.99 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (502 mg, 3.59 mmol, 1.2 eq) in a mixture of EtOH (10 mL), dioxane (20 mL) and H2O (10 mL) were added K2CO3 (142 mg, 1.03 mmol, 2.5 eq) and Pd(PPh3)4 (345 mg, 0.30 mmol, 0.1 eq). The mixture was heated at 85° C. overnight. The reaction was quenched by addition of 1M HCl and the aqueous phase extracted with EtOAc. The organic extract was dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography to give the title compound as a solid (558 mg, 73%).

Workup

customThe reaction was quenched by addition of 1M HCl
extractionthe aqueous phase extracted with EtOAc
extractionThe organic extract
dry with materialwas dried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-3c288aa163a147aba797e6b333fa82bc
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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