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

HRID 1821792ノート

反応式

HRID 1821792 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 220463764-Benzyloxymethyl-2-methoxy-1-nitro-benzene収率 84%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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): δ 7.85 (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).

後処理

  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

出典と根拠

ORDレコード
ord-5b9bd45166a2418e9362118064465109
出典データセット
uspto-grants-2009_10
特許番号
US07608618B2

反応ノート

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