Water → 2-Anilino-4-fluorobenzoic acid

HRID 1887825Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](Br)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(OCCO)C.[Cu].[Cu]I>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

Conditions

Temperature: 138 °C

Procedure

A mixture of 4-fluoro-2-bromo-benzoic acid (25 g, 114 mmol), aniline (12.5 mL, 137 mmol), potassium carbonate (17.4 g, 126 mmol), copper powder (725 mg, 11.4 mmol), and copper (I) iodide (1.09 g, 5.71 mmol) in 2-ethoxyethanol (70 mL) was stirred at 138° C. for 70 hr. under an argon atmosphere. The reaction mixture was cooled to room temperature, then water (60 mL) was added. The mixture was filtered through celite. The filtrate was adjusted to pH<2, then an additional 200 mL of water was added. The mixture was allowed to stir for 1 hr. The precipitated solids were collected via filtrated. The solids were taken up into 5% sodium carbonate solution, then filtered. The product was dried under vacuum overnight at 85° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe mixture was filtered through celite
additionan additional 200 mL of water was added
stirringto stir for 1 hr
customThe precipitated solids were collected
filtrationvia filtrated
filtrationfiltered
customThe product was dried under vacuum overnight at 85° C.

Sources & evidence

ORD record: ord-98ef912781b14a6882a0d75ea82ec416
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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