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

HRID 15618

反応式

HRID 15618 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3242c513a01a4e60ab44cd5f589c91bc
出典データセット
uspto-grants-2010_06
特許番号
US07732642B1

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