Sodium Hydroxide → 1-Bromo-3-methyl-5-nitro-2-vinylbenzene

HRID 1468705노트

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HRID 1468705 반응식
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[Br:17])(=O)=O.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC.[Li+].[Cl-].[OH-].[Na+]>CN(C=O)C>[Br:17][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[C:12]([CH3:13])[C:7]=1[CH:20]=[CH2:21]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 53438229Tri(butyl)vinyltinHCID 866997872-Bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate

생성물 1

HCID 866997861-Bromo-3-methyl-5-nitro-2-vinylbenzene수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

The reaction mixture of 2-bromo-6-methyl-4-nitrophenyl trifluoromethanesulfonate (65B) (10.1 g, 27.7 mmol), tributylvinyltin (8.18 ml, 27.7 mmol), LiCl (1.4 g, 33.2 mmol), PdCl2dppf (607 mg, 0.83 mmol) in DMF (50 ml) was reacted at 70° C. for 3 h. Then 2N NaOH was added and stirred at 70° C. for 5 min. The reaction mixture was cooled down, washed by sat. NaHCO3, extracted by EtOAc, dry over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in Hexanes to give 65C (1.9 g, 30%). 1H-NMR: 400 MHz, (CDCl3) δ: 8.30 (d, J=0.8 Hz, 1H), 8.03 (d, J=1 Hz, 1H), 6.71-6.64 (dd, J=18, 12 Hz, 1H), 5.77-5.74 (d, J=12 Hz, 1H), 5.51-5.46 (d, J=18 Hz, 1H), 2.48 (s, 3H).

후처리

  1. customwas reacted at 70° C. for 3 h
  2. temperatureThe reaction mixture was cooled down
  3. washwashed by sat. NaHCO3
  4. extractionextracted by EtOAc
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. custompurified by silica gel column
  9. washeluting by 0-100% EtOAc in Hexanes

출처 및 근거

ORD 기록
ord-1faa7832bde9447dbb9d270b9b89cf1e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006229B2

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