Water → Methyl 2-(4-bromothiophen-2-yl)acetate

HRID 714520

反応式

HRID 714520 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([O:9][CH3:10])=[O:8].[Al+3].[Cl-].[Cl-].[Cl-].[Br:15]Br.O>C(Cl)(Cl)Cl>[Br:15][C:4]1[CH:3]=[C:2]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[S:1][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 88055Methyl thiophen-2-acetateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 67367159Methyl 2-(4-bromothiophen-2-yl)acetate収率 41.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of methyl 2-(thiophen-2-yl)acetate (5 g, 32 m mol) and anhydrous AlCl3 (10.7 g, 80 mmol) in CHCl3 (50 ml) was added dropwise bromine (1.8 ml, 34 mmol) at 0˜5° C. over 30 min. When the addition was complete, the mixture was allowed to warm to room temperature overnight. Then it was poured into icy water (50 ml), extracted with EtOAc (30 ml×3). The combined organic phase was dried over Na2SO4, filtered and concentrated. Purification by column chromatography (PE/EtOAc=10/1) gave the product (3.1 g, 41%) as light yellow oil.

後処理

  1. additionWhen the addition
  2. extractionextracted with EtOAc (30 ml×3)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (PE/EtOAc=10/1)

出典と根拠

ORDレコード
ord-c684f8a700ae4cda99395bea95117d31
出典データセット
uspto-grants-2015_11
特許番号
US09187447B2

関連ノート

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