4-Methylmorpholine → (4-Bromo-phenyl)-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-methanone

HRID 1636726Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[O:11][CH3:12].C([Li])CCC.[Br:18][C:19]1[CH:30]=[CH:29][C:22]([C:23](N(OC)C)=[O:24])=[CH:21][CH:20]=1.BrC1C=CC(C(Cl)=O)=CC=1.Cl.CNOC.CN1CCOCC1.S([O-])(O)(=O)=O.[K+]>C1COCC1.CCCCCC.C(OCC)(=O)C>[Br:18][C:19]1[CH:30]=[CH:29][C:22]([C:23]([C:6]2[C:7]([F:8])=[C:2]([F:1])[C:3]([O:11][CH3:12])=[C:4]([F:10])[C:5]=2[F:9])=[O:24])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 5.4 g of 2,3,5,6-tetrafluoro-anisole in 80 ml of absolute THF is cooled to -78° C. and treated with 20.6 ml of 1.6M butyllithium in hexane within 15 min. After 20 min. 7.4 g of 4-bromo-N-methoxy-N-methylbenzamide (prepared from 4-bromo-benzoyl chloride and N,O-dimethylhydoxylamine.hydrochloride with N-methylmorpholine as the base) in 10 ml of THF are added dropwise and the mixture is stirred at -78° C. for 2 hrs. The reaction solution is poured into cold 10% potassium hydrogen sulphate solution/ethyl acetate and the organic phase is washed with water and 10% sodium chloride solution and dried. After crystallization from cyclohexane there are obtained 5.8 g of (4-bromo-phenyl)-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-methanone, m.p. 80-82° C.

Workup

additionare added dropwise
washthe organic phase is washed with water and 10% sodium chloride solution
customdried
customAfter crystallization from cyclohexane

Sources & evidence

ORD record: ord-884c0adc6c6e48c1af17604944955f6f
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034275

Reaction notes

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