Triethylamine → Perfluorophenyl 5-bromonaphthalene-2-sulfonate

HRID 1473296

반응식

HRID 1473296 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86687354Perfluorophenyl 5-bromonaphthalene-2-sulfonate수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-653192be75b8481e9e925bc2660974b0
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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