Triethylamine → perfluorophenyl 4-(2-chloro-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate

HRID 528516

반응식

HRID 528516 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([S:22](Cl)(=[O:24])=[O:23])[CH:20]=[CH:21][C:13]1=2.BrC1C=C(C(F)(F)F)C=CC=1N1CCOC2C=C(S(Cl)(=O)=O)C=CC1=2.ClC1C=C(C(F)(F)F)C=CC=1F.[F:63][C:64]1[C:69]([F:70])=[C:68]([F:71])[C:67]([F:72])=[C:66]([F:73])[C:65]=1[OH:74].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([S:22]([O:74][C:65]3[C:64]([F:63])=[C:69]([F:70])[C:68]([F:71])=[C:67]([F:72])[C:66]=3[F:73])(=[O:23])=[O:24])[CH:20]=[CH:21][C:13]1=2

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 897617224-(2-chloro-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride3회HCID 897618504-(2-Bromo-4-(Trifluoromethyl)Phenyl)-3,4-Dihydro-2H-Benzo[B][1,4]Oxazine-7-Sulfonyl Chloride

생성물 1

HCID 89761892perfluorophenyl 4-(2-chloro-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

INTERMEDIATE F was prepared from 4-(2-chloro-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (INTERMEDIATE E), which was prepared in an analogous fashion to INTERMEDIATE C, except using 2-chloro-1-fluoro-4-(trifluoromethyl)benzene instead of 2-bromo-1-fluoro-4-(trifluoromethyl)benzene in STEP 1. A 25 mL septa/cap vial under Argon was charged with INTERMEDIATE E (0.400 g, 0.970 mmol), and dissolved in DCM (3.6 mL). 2,3,4,5,6-Pentafluorophenol (PFP) (0.268 g, 1.456 mmol) was added, followed by dropwise addition of triethylamine (0.202 mL, 1.46 mmol). The reaction was stirred for 1 hour at room temperature. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 40% EtOAc:Heptane; product eluted at 30%) to afford perfluorophenyl 4-(2-chloro-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (0.543 g, 0.970 mmol) as a clear colorless oil. m/z (ESI) 391.8 (M-PFP)−.

후처리

  1. customA 25 mL septa/cap vial under Argon
  2. concentrationThe resulting material was concentrated
  3. dissolutiondissolved in minimal DCM
  4. custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 40% EtOAc:Heptane; product eluted at 30%)

출처 및 근거

ORD 기록
ord-24a699c574b34f44a4f2974177872d6d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

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