Water → HCID 57552297, compound

HRID 1666754Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[F:12][C:13]1[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH:20]=1)[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:21][C:3]2[CH:2]=[CH:7][C:6]([CH3:8])=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)=[C:17]([CH:20]=1)[C:18]#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 3-necked 5 L flask, equipped with a mechanic stirrer, a condenser, and a J-Kem temperature probe, a solution of 5-fluoro-2-nitrotoluene (158 g, 1.02 mol) in N,N-dimethylacetamide (500 mL) was added to a mixture of 5-fluoro-2-hydroxybenzonitrile (147 g, 1.07 mol) and potassium carbonate (163 g, 1.2 mol) in N,N-dimethylacetamide (573 mL) at room temperature. The mixture was heated to 100° C. After 8 hours, the reaction mixture was cooled to room temperature and water (3400 mL) was added in an ice bath. The precipitate was filtered, washed with water (1073 mL×2), and dried in vacuum (40° C.) to give (264 g, 90%) of the desired compound as a brown solid. MS (APCI−) m/z 272 (M−1) was detected. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, 1H, J=9 Hz), 7.41-7.48 (m, 1H), 7.38 (m, 1H), 7.07-7.14 (m, 1H), 6.88-7.10 (m, 1H), 2.63 (s, 3H).

Workup

customIn a 3-necked 5 L flask, equipped with a mechanic stirrer, a condenser
temperaturethe reaction mixture was cooled to room temperature
filtrationThe precipitate was filtered
washwashed with water (1073 mL×2)
customdried in vacuum (40° C.)

Sources & evidence

ORD record: ord-caecb9ad71e643c7b2b4d2f257f7a847
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044083B2

Reaction notes

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