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

HRID 879267ノート

反応式

HRID 879267 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 866997872-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-70 °C

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-26f825af12814bed84002ab7f91fbe4e
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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