Benzyl Bromide → 4-Benzyloxymethyl-2-methoxy-1-nitro-benzene

HRID 1830777노트

반응식

HRID 1830777 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH2:12][OH:13].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:20]([O:13][CH2:12][C:11]1[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[C:9]([O:8][CH3:7])[CH:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 6029613-Methoxy-4-nitrobenzyl alcohol

생성물 1

HCID 220463764-Benzyloxymethyl-2-methoxy-1-nitro-benzene수율 84%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a stirred suspension of finely powdered cesium carbonate (8.0 g, 24.5 mmol) was added 3-methoxy-4-nitrobenzyl alcohol (1.5 g, 8.18 mmol), followed by benzyl bromide, (2 mL, 16.4 mmol). After stirring at room temperature for 18 h, the suspension diluted with 100 mL diethyl ether, and washed with 3×50 mL water, then 50 mL brine. The organic phase was dried over MgSO4, filtered through a plug of silica, and concentrated. The resulting orange oil was purified by flash chromatography, eluting with 2:1 hexane-EtOAc, to give 1.87 g, (84%) of the benzyl ether. 1H NMR (400 MHz, CDCl3): δ7.85 (d, J=8.2 Hz, 1H) 7.3-7.4 (m, 5H), 7.26 (s, 1H), 6.97 (d, J=8.2 Hz, 1H), 4.61 (s, 2H), 4.59(s, 2H), 3.96 (s, 3H).

후처리

  1. washwashed with 3×50 mL water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe resulting orange oil was purified by flash chromatography
  6. washeluting with 2:1 hexane-EtOAc

출처 및 근거

ORD 기록
ord-906589697af34ea58501e4cde2f4b373
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067506B2

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