Water → 2-(4-Methoxyphenyl)benzonitrile

HRID 1954483

반응식

HRID 1954483 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 162722-BromobenzonitrileHCID 178491912HCID 178491912, 화합물

생성물 1

HCID 13933732-(4-Methoxyphenyl)benzonitrile수율 94%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4748a8aea93e43cfbe529d93cc49aef3
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121480

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