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

HRID 2306467ノート

反応式

HRID 2306467 の反応式
[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

参加物

11

反応物 7

HCID 79724-MethylmorpholineHCID 685154-Bromobenzoyl chlorideHCID 753512,3,5,6-TetrafluoroanisoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516920Potassium bisulfateHCID 109992524-Bromo-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 18434336(4-Bromo-phenyl)-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-methanone収率 53.3%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2f9dc2a41b3b46bd8d07e947635558b2
出典データセット
uspto-grants-2002_08
特許番号
US06441177B1

反応ノート

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