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

HRID 2060345

반응식

HRID 2060345 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

(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).

후처리

  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]

출처 및 근거

ORD 기록
ord-35f9a2459c0e4343ae5af26d3f52bed6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278356B2

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