Triethylamine → Methyl 4-bromo-1-benzothiophene-2-carboxylate

HRID 2183607

반응식

HRID 2183607 반응식
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].C(N(CC)CC)C.[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[CH:17]=O>CN(C)C=O>[Br:14][C:15]1[C:16]2[CH:17]=[C:2]([C:1]([O:5][CH3:6])=[O:4])[S:3][C:19]=2[CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 224739772-Bromo-6-fluorobenzaldehyde

생성물 1

HCID 22473901Methyl 4-bromo-1-benzothiophene-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
100 °C

실험 절차

Methyl thioglycolate (42.35 g) was added under nitrogen at 80° C. to a solution of triethylamine (109 ml) in dimethylformamide (290 ml), the mixture was stirred at 100° C. for 15 minutes, then a solution of 2-bromo-6-fluorobenzaldehyde (81.35 g; prepared in a manner similar to that described above) in dimethylformamide (70 ml) was added. The mixture was stirred at 130° C. for 5 hours, then it was cooled to ambient temperature and poured into ice-water (3000 ml). The resulting solid was collected by filtration, washed with water (2×250 ml) and dried in air to give methyl 4-bromobenzo[b]thiophene-2-carboxylate (101 g) as a yellow solid which was used without further purification.

후처리

  1. customprepared in a manner similar to
  2. additionwas added
  3. stirringThe mixture was stirred at 130° C. for 5 hours
  4. temperatureit was cooled to ambient temperature
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water (2×250 ml)
  7. customdried in air

출처 및 근거

ORD 기록
ord-d87411a842bc4219998c57a308c50d41
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900216B2

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