Triphenylphosphine → [1,1'-Biphenyl]-4-carbonitrile, 4'-(octyloxy)-

HRID 1954484

反応式

HRID 1954484 の反応式
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Pd](Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 178443728HCID 178443728、化合物

生成物 1

HCID 104173[1,1'-Biphenyl]-4-carbonitrile, 4'-(octyloxy)-収率 92%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-octyloxyphenylmagnesium bromide (124 g, 25% solution in tetrahydrofuran) is added dropwise over ten hours to a refluxing solution of 4-bromobenzonitrile (17 g), palladium (II) chloride (0.68 g) and triphenylphosphine (2.0 g) in tetrahydrofuran (100 ml). [HPLC: yield 92-94%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. Water (20 ml) and toluene (150 ml) are added and the mixture filtered hot (80-85 C.). The aqueous phase is separated off, and the solvent removed by distillation. The crude product is recrystallised from ethanol/n-hexane to give 4'-octyloxybiphenyl-4-carbonitrile as a solid. 1H NMR (CDCl3): 0.89(t,3H), 1.29-1.50(m,10H), 1.81(quint.2H), 4.00(t,2H), 6.99(d,2H), 7.52(d,2H), 7.63(d,2H), 7.68(d,2H).

後処理

  1. customis removed under vacuum
  2. additionWater (20 ml) and toluene (150 ml) are added
  3. filtrationthe mixture filtered hot (80-85 C.)
  4. customThe aqueous phase is separated off
  5. customthe solvent removed by distillation
  6. customThe crude product is recrystallised from ethanol/n-hexane

出典と根拠

ORDレコード
ord-c26bbe2ff1ba443fbc0c94b7c6a6112f
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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