Water → HCID 67357718, compound

HRID 1668344Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:18])=[CH:4][C:5](F)=[C:6]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[C:3]([F:18])=[CH:4][C:5]2[O:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH:9]=[N:8][C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 2-[[(5-bromo-2,4-difluorophenyl)imino]methyl]phenol (14.5 g, 46.5 mmol) in DMSO (0.43 L), K2CO3 (12.8 g, 71.8 mmol) and 18-Crown-6 (145 mg, 0.55 mmol) were added. The resulting mixture was stirred at 140° C. for 2.5 h and then allowed to cool to ambient temperature. Water (0.6 L) was added and the product was collected by filtration, washed with water and dried under reduced pressure to yield the title compound (15.7 g, 100%) which was used without further purification. 1H-NMR (400 MHz, CDCl3) 6.93-6.96 (d, J=8.2, 1H), 7.10-7.14 (d, J=8.2, 1H), 7.23-7.28 (m, 1H), 7.34-7.37 (m, 1H), 7.46-7.51 (m, 1H), 7.55-7.57 (d, J=7.8, 1H), 8.47 (s, 1H). (m/z)=292+294 (M+H)−.

Workup

temperatureto cool to ambient temperature
filtrationthe product was collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-a770803e2c194076a05573e0ea5013ee
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989442B2

Reaction notes

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