3-(4-Bromothiophenoxy)propionic acid → 6-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-one

HRID 619591노트

반응식

HRID 619591 반응식
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([S:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1>CS(O)(=O)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][CH2:7][CH2:8][C:9](=[O:11])[C:12]=2[CH:13]=1

참가 물질

4

반응물 1

HCID 167762423-(4-Bromothiophenoxy)propionic acid

생성물 1

HCID 139537366-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-one

시약·촉매·용매 2

HCID 962Water용매HCID 6395Methanesulfonic Acid용매

실험 절차

A solution of 3.63 g (13.9 mmol) of 3-(4-bromothiophenoxy)propionic acid in 60 ml methanesulfonic acid was heated to 75° C. for 1.5 hours. After cooling to room temperature the solution was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with 2N aqueous NaOH, H2O, and saturated aqueous NaCl and then dried over MgSO4. Removal of the solvent under reduced pressure afforded a yellow solid from which the product was isolated by column chromatography (3% hexanes) as a pale-yellow solid. 1H NMR (CDCl3): δ 8.22 (1H, d, J=2.1 Hz), 7.48 1H, dd, J=2.1, 8.3 Hz), 7.17 (1H, d, J=8.5 Hz), 3.24 (2H, t, J=6.4 Hz), 2.98 (2H, t, J=6.7 Hz).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with 2N aqueous NaOH, H2O, and saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent under reduced pressure
  5. customafforded a yellow solid from which the product

출처 및 근거

ORD 기록
ord-dcc9bae2a92c4dd3b5257facd60ebd1f
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958954

반응 노트

불러오는 중…