o-Fluorophenatole → HCID 68015073, compound

HRID 1913011Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[CH3:13].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([C:7]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:12][CH3:13])=[C:16]([F:21])[CH:17]=2)=[O:8])[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-bromo-2-chloro-benzoyl chloride 2a (12.4 g, 48.8 mmol) and 1-ethoxy-2-fluoro-benzene 4b (6.84 g, 48.8 mmol) were dissolved in 100 mL dichloromethane and cooled to 0° C., followed by addition of aluminum trichloride (5.86 g, 44 mmol) in batch. The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was partitioned after 20 mL 2 M hydrochloric acid was dropwise added in an ice bath. The aqueous phase was extracted with 30 mL dichloromethane and the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanone 4c (12.7 g, yellow solid), yield: 72.6%.

Workup

customThereafter, the reaction mixture was partitioned after 20 mL 2 M hydrochloric acid
additionwas dropwise added in an ice bath
extractionThe aqueous phase was extracted with 30 mL dichloromethane
extractionthe organic extract
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-59775cbdc62d4b0c95d2dfb6649bc051
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609622B2

Reaction notes

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