Water → Methyl 1-(4-amino-3-bromophenyl)cyclopropanecarboxylate

HRID 468288ノート

反応式

HRID 468288 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.O>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:6][C:7]=1[Br:22]

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58841079Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylate

生成物 1

HCID 59129194Methyl 1-(4-amino-3-bromophenyl)cyclopropanecarboxylate収率 78.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of methyl 1-(4-aminophenyl)cyclopropanecarboxylate (10.38 g, 0.05 mol) in acetonitrile (200 mL) was added NBS (9.3 g, 0.05 mol) at room temperature. The mixture was stirred overnight. Water (200 mL) was added. The organic layer was separated and the aqueous phase was extracted with EtOAc (80 mL×3). The organic layers were dried with anhydrous Na2SO4 and evaporated to give methyl 1-(4-amino-3-bromophenyl)cyclopropanecarboxylate (10.6 g, 78%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=2.0 Hz, 1H), 7.08 (dd, J=1.6, 8.4 Hz, 1H), 6.70 (d, J=8.4 Hz, 1H), 3.62 (s, 3H), 1.56-1.54 (m, 2H), 1.14-1.11 (m, 2H).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (80 mL×3)
  3. dry with materialThe organic layers were dried with anhydrous Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-ec4d16a02f8148099198a4356f03a7da
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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