Triethylamine → Perfluorophenyl 5-bromonaphthalene-2-sulfonate

HRID 1473296

反応式

HRID 1473296 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:7]2.S(Cl)(Cl)=O.[F:20][C:21]1[C:26]([F:27])=[C:25]([F:28])[C:24]([F:29])=[C:23]([F:30])[C:22]=1O.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][C:22]1[C:23]([F:30])=[C:24]([F:29])[C:25]([F:28])=[C:26]([F:27])[C:21]=1[F:20])(=[O:14])=[O:13])=[CH:7]2

参加物

6

反応物 4

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 24386Thionyl ChlorideHCID 99040065-bromonaphthalene-2-sulfonic Acid

生成物 1

HCID 86687354Perfluorophenyl 5-bromonaphthalene-2-sulfonate収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 15-mL round-bottom flask was charged with 5-bromonaphthalene-2-sulfonic acid (2.346 g, 8.17 mmol) and DMF (8.17 mL) to give a green suspension. Thionyl chloride (1.193 mL, 16.34 mmol) was added dropwise, and the resulting orange mixture was stirred for 2 h. The mixture was poured into ice and extracted with DCM (three times). The combined organic extracts were washed with water, dried over sodium sulfate, filtered and concentrated. The residue was dissolved in DCM (35 mL), and the resulting solution was added to 2,3,4,5,6-pentafluorophenol (2.256 g, 12.26 mmol). Triethylamine (1.708 mL, 12.26 mmol) was added dropwise, and the resulting mixture was stirred for 30 min and then concentrated. The residue was taken up in DCM and filtered. The filtrate was concentrated, and the product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane) to afford perfluorophenyl 5-bromonaphthalene-2-sulfonate (2.4426 g, 5.39 mmol) as a light-yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.64-8.46 (m, 2H), 8.13-7.95 (m, 3H), 7.63-7.47 (m, 1H).

後処理

  1. customto give a green suspension
  2. additionThe mixture was poured into ice
  3. extractionextracted with DCM (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in DCM (35 mL)
  9. stirringthe resulting mixture was stirred for 30 min
  10. concentrationconcentrated
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated
  13. customthe product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-653192be75b8481e9e925bc2660974b0
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

関連ノート

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