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

HRID 1014235ノート

反応式

HRID 1014235 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 220516194-(Chloromethyl)-2-methoxy-1-nitrobenzene収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9cfeaedb58b24281828433bccebc05f8
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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