Nitromethane → HCID 86730326, compound

HRID 1427025Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH:18]([F:20])[F:19])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:26]([CH3:29])([O-:28])=[O:27]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:29]/[N+:26]([O-:28])=[O:27])[CH:14]=[CH:15][C:16]=1[O:17][CH:18]([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

3-(Benzyloxy)-4-(difluoromethoxy)benzaldehyde described in Production Example 19-2 (3.94 g, 14.2 mmol) was dissolved in acetic acid (11 mL), then ammonium acetate (1.27 g, 16.4 mmol) and nitromethane (1.9 mL, 35.1 mmol) were added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 130° C. for 2 hours. The mixture was cooled to room temperature and then heated and stirred at 130° C. again for 1 hour. The precipitate was collected by filteration and washed with a liquid mixture of acetic acid and ethanol to obtain the title compound (2.36 g, 52%). The filtrate was dissolved in dichloromethane and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-4:1), and then the target fraction was concentrated under vacuum. The precipitate was washed with ethanol to obtain the title compound (406 mg, 8.9%).

Workup

temperaturethe mixture was heated
temperatureThe mixture was cooled to room temperature
temperatureheated
stirringstirred at 130° C. again for 1 hour
customThe precipitate was collected by filteration
washwashed with a liquid mixture of acetic acid and ethanol

Sources & evidence

ORD record: ord-ff99f68533c64a299e06c0f8a983ac32
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

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