Water → 2-(4-Methoxyphenyl)benzonitrile

HRID 1954483

反応式

HRID 1954483 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.Br[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1.[Pd](Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:12]2[C:13]([C:14]#[N:15])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 162722-BromobenzonitrileHCID 178491912HCID 178491912、化合物

生成物 1

HCID 13933732-(4-Methoxyphenyl)benzonitrile収率 94%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-methoxyphenylmagnesium bromide (280 g, 15% solution in tetrahydrofuran) is added dropwise over seven hours to a refluxing solution of 2-bromobenzonitrile (32 g), palladium (II) chloride (1.3 g) and triphenylphosphine (3.8 g) in tetrahydrofuran (210 ml). [HPLC: yield 94-95%]. After cooling to room temperature and the addition of water (50 ml), tetrahydrofuran is removed under vacuum. The residue is extracted with toluene (230 ml). Insoluble material is filtered off and the solvent distilled off. The crude product is recrystallised from ethanol to give 4'-methoxybiphenyl-2-carbonitrile as a solid, m.pt. 82-83° C. 1H NMR (CDCl3): 3.90(s,3H), 7.02(d,2H), 7.36-7.52(m,4H), 7.59-7.65(m,1H), 7.74(d,1H).

後処理

  1. customis removed under vacuum
  2. extractionThe residue is extracted with toluene (230 ml)
  3. filtrationInsoluble material is filtered off
  4. distillationthe solvent distilled off
  5. customThe crude product is recrystallised from ethanol

出典と根拠

ORDレコード
ord-4748a8aea93e43cfbe529d93cc49aef3
出典データセット
uspto-grants-2000_09
特許番号
US06121480

関連ノート

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