Sodium Hydroxide → 2,3,5,6-Tetrafluoro-[1,1'-biphenyl]-4-carboxylic acid

HRID 1470618Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([F:19])[C:6]=1[F:20])=[O:4].[OH-].[Na+]>O1CCCC1>[F:12][C:9]1[C:10]([F:11])=[C:5]([C:3]([OH:4])=[O:2])[C:6]([F:20])=[C:7]([F:19])[C:8]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 2,3,5,6-tetrafluoro-biphenyl-4-carboxylic acid methyl ester (20 g, 70.4 mmol) in tetrahydrofuran (350 mL) was added an aq, solution of 5 N sodium hydroxide (150 mL). The reaction mixture refluxed with stirring for 4 hours. Progress of the reaction was monitored by TLC. The reaction mixture was then concentrated and the resulting residue was cooled to 10° C. and acidified with an aq. Solution of 50% HCl. The formed precipitate was filtered, washed thoroughly with water and dried to obtain title compound as colorless solid (17 g, 89.4%).

Workup

temperatureThe reaction mixture refluxed
concentrationThe reaction mixture was then concentrated
filtrationThe formed precipitate was filtered
washwashed thoroughly with water
customdried

Sources & evidence

ORD record: ord-d6ed55366f154cd0af1381bc29b3293a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006454B2

Reaction notes

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