Triphenylphosphine → 4-(4-Chlorophenyl)benzonitrile

HRID 1954485

反応式

HRID 1954485 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Cl)=[CH:4][CH:3]=1.Br[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Pd](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 178478983HCID 178478983、化合物

生成物 1

HCID 13943084-(4-Chlorophenyl)benzonitrile収率 75%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-chlorophenylmagnesium chloride (114 g, 18% solution in tetrahydrofuran) is added dropwise over seven hours to a refluxing solution of 4-bromobenzonitrile (20 g), palladium (II) chloride (0.78 g ) and triphenylphosphine (2.3 g) in tetrahydrofuran (100 ml). [HPLC: yield 75-79%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. The residue is taken up in toluene/water (1:1) (200 ml) and filtered. The aqueous phase is separated off, and the solvent removed by distillation. The crude product is recrystallised from isopropanol/ethanol to give 4'-chlorobiphenyl-4-carbonitrile as a solid, m.pt. 128-130° C. 1H NMR (CDCl3): 2.41(s,3H), 7.46(d,2H), 7.53(d,2H), 7.65(d,2H), 7.74(d,2H).

後処理

  1. customis removed under vacuum
  2. filtrationfiltered
  3. customThe aqueous phase is separated off
  4. customthe solvent removed by distillation
  5. customThe crude product is recrystallised from isopropanol/ethanol

出典と根拠

ORDレコード
ord-d37c410c20a94ee0802651aebd966662
出典データセット
uspto-grants-2000_09
特許番号
US06121480

関連ノート

読み込み中…