4-Nitrobenzonitrile → Benzonitrile, 4-(2,2,2-trifluoro-1,1-dimethylethoxy)-

HRID 911269

反応式

HRID 911269 の反応式
[F:1][C:2]([F:8])([F:7])[C:3]([OH:6])([CH3:5])[CH3:4].[H-].[Na+].[N+]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)([O-])=O>CN(P(N(C)C)(N(C)C)=O)C.C(OCC)C>[F:1][C:2]([F:8])([F:7])[C:3]([CH3:5])([CH3:4])[O:6][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 120904-NitrobenzonitrileHCID 24758Sodium hydrideHCID 681821,1,1-Trifluoro-2-methylpropan-2-ol

生成物 1

HCID 13440336Benzonitrile, 4-(2,2,2-trifluoro-1,1-dimethylethoxy)-収率 25.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

Add 2-trifluoromethyl-2-propanol (3.4 g, 27 mmol) slowly to a slurry of sodium hydride (0.6 g, 60% in mineral oil, washed with hexane) in HMPA (5 mL) under nitrogen. Stir the slurry for 15 min and add a solution of 4-nitrobenzonitrile (2.0 g, 13.5 mmol) in HMPA (10 mL). Stir the resulting purple slurry at ambient temperature for 16 h, dilute with diethyl ether (100 mL) and wash with 5% aqueous HCl (30 mL). Separate the layers and extract the aqueous layer with diethyl ether (2×50 mL). Combine the organic extracts and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1) to obtain the desired intermediate (780 mg, 25%). GC-MS m/z: 229 (M+).

後処理

  1. stirringStir the resulting purple slurry at ambient temperature for 16 h
  2. washwash with 5% aqueous HCl (30 mL)
  3. customSeparate the layers
  4. extractionextract the aqueous layer with diethyl ether (2×50 mL)
  5. concentrationCombine the organic extracts and concentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1)

出典と根拠

ORDレコード
ord-d976a0521a8f4b87bac0519b7764704d
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

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