Hydrochloric Acid → 3-Chloro-4-(1,3-difluoropropan-2-yloxy)benzoic acid

HRID 515753Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH2:16][F:17])[CH2:14][F:15])[C:5]([O:7]C)=[O:6].[Li+].[OH-].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH2:14][F:15])[CH2:16][F:17])[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of methyl 3-chloro-4-(1,3-difluoropropan-2-yloxy)benzoate (2.00 g, 7.56 mmol) in dioxane (15.11 mL) was added LiOH (1.0 M aq, 22.67 mL, 22.67 mmol). The reaction was stirred at 30° C. for 1.5 h in a 1 L round-bottomed flask. The reaction was cooled to room temperature and poured into 1 N HCl. A precipitate was formed and filtered by vacuum filtration to give the title compound (1.5 g) as a white solid. LCMS m/z=250.9 [M+H]+.

Workup

temperatureThe reaction was cooled to room temperature
customA precipitate was formed
filtrationfiltered by vacuum filtration

Sources & evidence

ORD record: ord-fd0196bb22364715b4baaa4a74bc5f29
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108969B2

Reaction notes

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