Hydrochloric Acid → (5-Bromo-2-thienyl)(4-ethylphenyl)methanone

HRID 1270678ノート

反応式

HRID 1270678 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)[CH3:6].[Br:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.Cl>ClCCl>[Br:16][C:17]1[S:18][C:19]([C:11]([C:10]2[CH:14]=[CH:15][C:7]([CH2:5][CH3:6])=[CH:8][CH:9]=2)=[O:12])=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 138512-BromothiopheneHCID 853684-Ethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 43462872(5-Bromo-2-thienyl)(4-ethylphenyl)methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Aluminum chloride (8.9 g) and 4-ethylbenzoylchloride (5.96 g) were added to a solution of 2-bromothiophene (3.2 ml) in dichloromethane (50 ml) at 0° C., and the mixture was stirred for four hours at room temperature. 10% hydrochloric acid was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water- and saturated saline solution in order and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (5-bromo-2-thienyl)(4-ethylphenyl) methanone (8.97 g). Borontrifluoride diethyl ether complex (1.57 ml) and triethylsilane (3.83 ml) were added to a solution of (5-bromo-2-thienyl) (4-ethylphenyl) methanone in acetonitrile (20 ml) at −40° C., and the mixture was stirred for two hours. Aqueous solution of saturated potassium carbonate was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 2-bromo-(4-ethylbenzyl)thiophene (6.78 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water- and saturated saline solution in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated from the filtrate under reduced pressure
  6. customto give the residue
  7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-0421f56075e447d5a0eb631683b75206
出典データセット
uspto-grants-2007_04
特許番号
US07202350B2

反応ノート

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