Hydrochloric Acid → 2-[2-(4-Fluorophenyl)ethyl]-5-fluorobenzoic Acid

HRID 8397Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=2[C:12]#N)=[CH:4][CH:3]=1.[OH-:19].[Na+].[OH2:21].Cl>C(O)CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=2[C:12]([OH:21])=[O:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-fluorobenzonitrile (2.12 g, 8.72 mmol, 1 equiv) and aq. NaOH (10N; 3.9 mL, 39.3 mmol, 4.5 equiv) in ethylene glycol (25 mL) was heated at 190° C. for 24 h. After allowing the mixture to cool, H2O (100 mL) was added followed by 12N HCl (8 mL). The cloudy mixture precipitated the desired product as a cream-colored solid. This material was washed with H2O (3×20 mL) and dried under vacuum (18 h, 25° C., 0.1 mm Hg) to provide 2.02 g (88.4%) of a cream-colored solid.

Workup

temperatureto cool
customThe cloudy mixture precipitated the desired product as a cream-colored solid
washThis material was washed with H2O (3×20 mL)
customdried under vacuum (18 h, 25° C., 0.1 mm Hg)

Sources & evidence

ORD record: ord-46f23c8aa8a04871bdab7af10a51daaf
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087765B2

Reaction notes

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