Hydrochloric Acid → 2-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate

HRID 879267노트

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HRID 879267 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[OH:12].CCN(CC)CC.[O:20](S(C(F)(F)F)(=O)=O)[S:21]([C:24]([F:27])([F:26])[F:25])(=O)=[O:22].Cl>C(Cl)Cl>[F:25][C:24]([F:27])([F:26])[S:21]([O:12][C:3]1[C:4]([CH3:11])=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])(=[O:22])=[O:20]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 203754122-Bromo-6-methyl-4-nitrophenol

생성물 1

HCID 866997872-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-70 °C

실험 절차

To a solution of 2-bromo-6-methyl-4-nitrophenol (110.0 g, 0.474 mol) in DCM (950 mL) at −70° C. was added Et3N (62.3 g, 0.616 mol) and Tf2O (147.1 g, 0.521 mol). The resulting solution was stirred at −70° C. for 20 min. TLC showed the reaction was complete. Aqueous HCl (0.5 M, 1 L) was added to quench the reaction. The DCM layers were separated, dried over anhydrous Na2SO4, filtered, concentrated in vacuo and purified by silica gel column (Petroleum Ether→Petroleum Ether:EtOAc (20:1)) to afford desired 2-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate (146.7 g, 85%) as yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 8.41 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.8 Hz, 1H), 2.59 (s, 3H).

후처리

  1. customto quench
  2. customthe reaction
  3. customThe DCM layers were separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column (Petroleum Ether→Petroleum Ether:EtOAc (20:1))

출처 및 근거

ORD 기록
ord-26f825af12814bed84002ab7f91fbe4e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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