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

HRID 619591ノート

反応式

HRID 619591 の反応式
[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

参加物

4

反応物 1

HCID 167762423-(4-Bromothiophenoxy)propionic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6395Methanesulfonic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dcc9bae2a92c4dd3b5257facd60ebd1f
出典データセット
uspto-grants-1999_09
特許番号
US05958954

反応ノート

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