Potassium Carbonate → 4-((6-Bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)benzamide

HRID 2171113Notes

Reaction equation

[Br:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[C:5]([O:11][CH:12]([F:14])[F:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=1>C(#N)C>[Br:1][C:2]1[C:7]([O:8][CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=2)=[C:6]([O:9][CH3:10])[C:5]([O:11][CH:12]([F:13])[F:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 6-bromo-3-(difluoromethoxy)-2-methoxyphenol (1.0 g, 3.71 mmol) in acetonitrile (10 mL) was added potassium carbonate (1.53 g, 11.08 mmol) and 4-(bromomethyl)benzamide (795 mg, 3.71 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure to afford 4-((6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)benzamide as a solid (1 g, 67%).

Workup

customthe resultant reaction mixture
temperatureThe reaction mixture was cooled to RT
filtrationfiltered through celite
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-d00a7c62afaf450ab3e122bbe0504926
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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