Nitrogen → Methyl 2-(5-bromothiophen-2-yl)acetate

HRID 2060345

反応式

HRID 2060345 の反応式
N#N.[CH3:3][O:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:3][O:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][C:9]([Br:13])=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 947NitrogenHCID 67184N-bromobutanimideHCID 88055Methyl thiophen-2-acetate

生成物 1

HCID 12403315Methyl 2-(5-bromothiophen-2-yl)acetate収率 81.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

(The following reaction is carried out in an anhydrous N2 atmosphere.) Dissolve thiophene-2-yl-acetic acid methyl ester (42) (2.0 g, 12.8 mmol) in anhydrous chloroform (9.0 mL) and glacial acetic acid (9.0 mL), add N-bromosuccinimide (2.3 g, 13.0 mmol) in portions and stir the mixture for 3 d at rt. Add water to the reaction mixture, separate layers and extract the aqu. layer with dichloromethane. Wash combined organic layer several times with a 1 M aqu. NaOH and water and once with brine and dry it with Na2SO4. Purify the crude product by preparative radial chromatography (CyH/EtOAc 5+1] to obtain (5-bromo-thiophen-2-yl)-acetic acid methyl ester (43) as a yellow oil (2.46 g, 81%) which is used without any further purification. 1H NMR (400 MHz, CDCl3): 3.71 (s, 3H); 3.75 (s, 2H); 6.67 (d, 1H, J=3.8 Hz); 6.88 (d, 1H, J=3.8 Hz).

後処理

  1. custom(The following reaction
  2. customAdd water to the reaction mixture, separate layers
  3. extractionextract the aqu
  4. washWash
  5. dry with materialNaOH and water and once with brine and dry it with Na2SO4
  6. customPurify the crude product by preparative radial chromatography (CyH/EtOAc 5+1]

出典と根拠

ORDレコード
ord-35f9a2459c0e4343ae5af26d3f52bed6
出典データセット
uspto-grants-2012_10
特許番号
US08278356B2

関連ノート

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