Oxalyl chloride → Methyl 2-bromothiophene-3-carboxylate

HRID 604362노트

반응식

HRID 604362 반응식
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].[C:10](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 123209712-Bromo-3-thiophenecarboxylic acid

생성물 1

HCID 53302196Methyl 2-bromothiophene-3-carboxylate수율 98.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

2-bromo-3-thiophene carboxylic acid (1.0 eq, 12.56 g, 60.66 mmol) was suspended in CH2Cl2 (200 ml). Oxalyl chloride (1.1 eq, 5.9 ml, 67.16 mmol) and 5 drops of DMF were added, inducing formation of gas. The mixture was stirred overnight at room temperature and the volatiles were removed in vacuo. The resulting solid was suspended in dry methanol (150 ml) and the mixture heated to ebullition. Evaporation of the solvents afforded methyl 2-bromo-3-thiophene carboxylate (13.16 g, 98% yield) as a crude brown oil. LCMS (ES): 99% pure, m/z not detected; 1H NMR (CDCl3, 400 MHz) δ 3.88 (s, 3H), 7.23 (d, J=5.6, 1H), 7.56 (d, J=5.6, 1H) ppm.

후처리

  1. customthe volatiles were removed in vacuo
  2. temperaturethe mixture heated to ebullition
  3. customEvaporation of the solvents

출처 및 근거

ORD 기록
ord-4b1289f312a6478c94e85d2d5f89a29f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910600B2

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