Potassium Carbonate → HCID 23001837, 화합물

HRID 398090노트

반응식

HRID 398090 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[OH:11][C:12]1[CH:13]=[CH:14][C:15]2[S:19][CH2:18][CH2:17][C:16]=2[CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:19][CH2:18][CH2:17][C:16]=3[CH:20]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 11367101Benzo[b]thiophene-5-ol, 2,3-dihydro-

생성물 1

HCID 23001837HCID 23001837, 화합물수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5-bromo-2-fluorobenzaldehyde (1.08 g, 5.32 mmol), 5-hydroxy-2,3-dihydrobenzothiophene (prepared as described in Synth. Commun. 1991, 21, 959-964) (808 mg, 5.31 mmol) and K2CO3 (1.47 g, 10.6 mmol) in DMF (5 mL) was heated at 90° C. for 16 h. After cooling to room temperature the mixture was partitioned between water (50 mL) and ether (50 mL), the aqueous layer being extracted with ether (50 mL). The combined organic extracts were washed with water (50 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography [SiO2; 9:1 (pentane/EtOAc)], then triturated with ether, to give the product (1.1 g, 62%) as a pale yellow solid; δH (CDCl3, 400 MHz) 3.28 (2H, t), 3.41 (2H, t), 6.78 (1H, d), 6.84 (1H, d), 6.92 (1H, s), 7.20 (1H, d), 7.58 (1H, d), 8.00 (1H, s), 10.43 (1H, s).

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas partitioned between water (50 mL) and ether (50 mL)
  3. extractionthe aqueous layer being extracted with ether (50 mL)
  4. washThe combined organic extracts were washed with water (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography [SiO2; 9:1 (pentane/EtOAc)]
  8. customtriturated with ether

출처 및 근거

ORD 기록
ord-ee49d599641040919758821b012e0af9
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610747B2

반응 노트

불러오는 중…