2,4,6-Trimethylphenol → 4-(2,4,6-Trimethylphenoxy)benzonitrile

HRID 15618

반응식

HRID 15618 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[K+].[Br-]>C1(C)C=CC=CC=1.CN1C(=O)CCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 106982,4,6-TrimethylphenolHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 253877Potassium Bromide

생성물 1

HCID 222423224-(2,4,6-Trimethylphenoxy)benzonitrile수율 97%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
140 °C

실험 절차

Into a 250 mL three-necked, round-bottomed flask equipped with a magnetic stir-bar, nitrogen inlet, and a condenser, 2,4,6-trimethylphenol (6.00 g, 44.1 mmol), 4-fluorobenzonitrile (5.34 g, 44.1 mmol), potassium carbonate (7.30 g, 52.8 mmol), and a mixture of NMP (100 mL) and toluene (60 mL) were placed. The reaction mixture was then heated and maintained around 140° C. for 8 h with vigorous nitrogen flow. The dark solution was filtered while it was warm and the filtrate was poured into distilled water containing 5% hydrochloric acid. The solution was separated into organic layer and aqueous layer. The organic layer was diluted with dichloromethane and separated. The solvent was removed to dryness. Light brown oily residue was freeze-dried to afford 10.1 g (97% yield): Anal. Calcd. for C16H15NO: C, 80.98%; H, 6.37%; N, 5.90%; O, 6.74%. Found: C, 80.31%; H, 6.37%; N, 5.75%; O, 6.46%. FT-IR (KBr, cm−1): 2226 (C≡N stretch). Mass spectrum (m/e): 237 (M+, 100% relative abundance), 222, 204, 194. 1H NMR (CDCl3, ppm) δ 2.05 (s, 6H, CH3), 2.30 (s, 3H, CH3), 6.81-6.84 (d, 2H, Ar), 6.91 (s, 2H, Ar), 7.53-7.56 (d, 2H, Ar). 13C NMR (CDCl3, ppm) δ 16.10, 20.79, 115.48, 129.07, 129.15, 129.88, 130.48, 134.25, 147.84, 150.03, 161.44.

후처리

  1. customInto a 250 mL three-necked, round-bottomed flask equipped with a magnetic stir-bar, nitrogen inlet, and a condenser
  2. temperatureThe reaction mixture was then heated
  3. filtrationThe dark solution was filtered while it
  4. temperaturewas warm
  5. additionthe filtrate was poured
  6. distillationinto distilled water containing 5% hydrochloric acid
  7. customThe solution was separated into organic layer and aqueous layer
  8. additionThe organic layer was diluted with dichloromethane
  9. customseparated
  10. customThe solvent was removed to dryness
  11. customLight brown oily residue was freeze-dried
  12. customto afford 10.1 g (97% yield)

출처 및 근거

ORD 기록
ord-3242c513a01a4e60ab44cd5f589c91bc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732642B1

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