Ammonium Hydroxide → Methyl 4-(2-cyanophenyl)benzoate

HRID 1422350ノート

反応式

HRID 1422350 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([Li])(C)(C)C.[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.[OH-].[NH4+]>C1COCC1.CCCCC.[Cl-].[Zn+2].[Cl-].[Ni].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:20][CH:19]=1

参加物

9

反応物 4

HCID 14923Ammonium HydroxideHCID 162722-BromobenzonitrileHCID 69273Methyl 4-iodobenzoateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 1393412Methyl 4-(2-cyanophenyl)benzoate

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 57357981bis(triphenylphosphine) Nickel触媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of 2-bromobenzonitrile (1.00 g, 5.494 mmol), in THF (16.5 mL) at -100° C. was added t-butyl lithium (6.46 mL, of a 1.7M solution in pentane, 10.98 mmol. After 5 minutes zinc chloride(5.494 mL, of a 1M solution in THF, 5.494 mmol) was added. The reaction was stirred for 10 minutes at -78° C. and then allowed to warm to 0° C. and stirred for 1 hour. This solution was added via cannula to a solution of methyl-4-iodobenzoate (1.44 g, 5.494 mmol) and bis(triphenylphosphine) Nickel II chloride (0.359 g, 0.549 mmol) in THF (12 mL). The reaction stirred for 1 hour at 0° C. and then at ambient temperature for a further 16 hours. Saturated ammonium hydroxide solution (5 mL) was added and the mixture stirred until homogenous, extracted with EtOAc and the organic extracts washed with saturated brine, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (Silica gel, 50% CH2Cl2 to 50%) EtOAc in hexanes) to afford the title compound.

後処理

  1. temperatureto warm to 0° C.
  2. stirringstirred for 1 hour
  3. stirringThe reaction stirred for 1 hour at 0° C.
  4. waitat ambient temperature for a further 16 hours
  5. stirringthe mixture stirred until homogenous,
  6. extractionextracted with EtOAc
  7. washthe organic extracts washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customThe residue was chromatographed (Silica gel, 50% CH2Cl2 to 50%) EtOAc in hexanes)

出典と根拠

ORDレコード
ord-1c27247b605145caa47f43b3a10ab840
出典データセット
uspto-grants-2000_06
特許番号
US06080870

反応ノート

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