Sodium Carbonate → 4-(Chloromethyl)-2-methoxy-1-nitrobenzene

HRID 1014235노트

반응식

HRID 1014235 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:33]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6][Cl:33]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 6029613-Methoxy-4-nitrobenzyl alcohol

생성물 1

HCID 220516194-(Chloromethyl)-2-methoxy-1-nitrobenzene수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-methoxy-4-nitrobenzyl alcohol (3.0 g, 16.4 mmol) in 150 mL of dichloromethane was added triphenylphosphine (5.6 g, 21.3 mmol). The reaction was cooled to 0° C. and N-chlorosuccinimide (2.8 g, 21.3 mmol) was added. The reaction was warmed to room temperature and then heated gently to 50° C. for 2 h. The reaction was poured into aqueous sodium carbonate solution and the aqueous layer was extracted with dichloromethane and then ethyl acetate. Combined organics were dried over anhydrous MgSO4, filtered, concentrated onto silica gel and purified by flash chromatography with ethyl acetate/hexanes as the eluent to afford 3-methoxy-4-nitrobenzyl chloride (2.76 g, 84%). 1H NMR (400 MHz, CDCl3) δ ppm 7.88 (d, J=8.2 Hz, 1H), 7.44 (d, J=1.6 Hz, 1H), 7.17 (d, J=8.2, 1.7 Hz, 1H), 4.81 (s, 2H), 3.91 (s, 3H).

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. temperatureheated gently to 50° C. for 2 h
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialCombined organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. custompurified by flash chromatography with ethyl acetate/hexanes as the eluent

출처 및 근거

ORD 기록
ord-9cfeaedb58b24281828433bccebc05f8
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

반응 노트

불러오는 중…