Water → 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-2H-chromene-3-carbaldehyde

HRID 217444Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH2:8][O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1[C:32]([F:35])([F:34])[F:33].O>CN(C=O)C>[F:33][C:32]([F:34])([F:35])[C:23]1[CH:24]=[C:25]([C:28]([F:31])([F:29])[F:30])[CH:26]=[CH:27][C:22]=1[CH2:21][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-Hydroxy-2H-chromene-3-carbaldehyde (200 mg) was dissolved in DMF (5 mL), and K2CO3 (235 mg) and 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (0.234 mL) were added thereto, followed by stirring at 80° C. for 30 minutes. The reaction liquid was poured into water, and the resulting powder was collected by filtration and dried under reduced pressure to obtain 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-2H-chromene-3-carbaldehyde (455 mg) as a pale yellow powder.

Workup

customThe reaction liquid
filtrationthe resulting powder was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-bb615ba9c64f4c8c80c17cc037fc6111
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193378B2

Reaction notes

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