1,2-Dibromoethane → Benzene, 2-(2-bromoethoxy)-4-methyl-1-nitro-

HRID 322609

반응식

HRID 322609 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[Br:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:12][CH2:13][CH2:14][O:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresol

생성물 1

HCID 13685252Benzene, 2-(2-bromoethoxy)-4-methyl-1-nitro-수율 115.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

122.5 g (800 mmol) 5-methyl-2-nitrophenol, 751.0 g (4000 mmol) 1,2-dibromoethane, 110.7 g (800 mmol) K2CO3 were suspended in 400 ml anhydrous DMF. The suspension was heated at 120° C. for 1 hour, then cooled and most of the liquid was evaporated. The residue was dissolved in 1 l CHCl3 and 1 l water. The organic layer was washed with 2×1 l of 1.8% NaOH till the aqueous layer became pale yellow. The organic layer was dried over Na2SO4 for 18 h, filtered and the solvent was evaporated to give ˜240 g oil. The oil was triturated with 240 ml boiling methanol and allowed to settle for 2 h. The resultant precipitate was filtered, washed with 2×100 ml cold methanol and dried at RT for 18 h to afford 89.4 g (43%) off-white crystal. H1NMR (CDCl3) δ (ppm): 2.40(s, 3H), 3.65(t,2H), 4.30(t,2H), 6.85(d,2H), 7.75(d,1H).

후처리

  1. temperaturecooled and most of the liquid
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in 1 l CHCl3
  4. washThe organic layer was washed with 2×1 l of 1.8% NaOH till the aqueous layer
  5. dry with materialThe organic layer was dried over Na2SO4 for 18 h
  6. filtrationfiltered
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-e281d559eef24698a3ec34a00625fabe
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211359B1

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