4-Chloroanisole → 1,1'-Biphenyl, 4,4'-dimethoxy-

HRID 1596849

反応式

HRID 1596849 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[F-].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[CH:3][CH:4]=1

参加物

6

反応物 3

HCID 121674-ChloroanisoleHCID 25953Cesium fluorideHCID 201262(4-Methoxyphenyl)boronic acid

生成物 1

HCID 164841,1'-Biphenyl, 4,4'-dimethoxy-収率 99.1%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

In the drybox, 20.0 mg (0.0876 mmol) of (Me2CH)PH(O)(2,4-(MeO)2C6H3) from Experiment 3, 20 mg (0.0218 mm) of Pd2(dba)3 and 5.0 mL of 1,4-dioxane were loaded into a reactor (20 ml) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature overnight. Next, 143.0 mg (1.0 mm) of 4-chloroanisole, 228 mg (1.5 mm) of 4-MeOC6H4B(OH)2 and 456 mg (3.0 mmol) of CsF were added into the reactor. The resulting mixture was refluxed for 60 h. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using ethyl acetate/hexane (5% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 213 mg (99% yield) of p-(4-methoxyphenyl)anisole. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.38 (d, J=8.68 Hz, 4H), 6.86 (d, J=8.68 Hz, 4H), 3.74 (s, 6H) ppm. 13C NMR (125 MHz, CDCl3): δ 158.7, 133.5, 127.7, 114.2, 55.3 ppm. Anal Calcd for C14H14O2: C, 78.48; H, 6.59. Found: C, 78.44; H, 6.53.

後処理

  1. custom(20 ml) equipped with a magnetic stir bar
  2. temperatureThe resulting mixture was refluxed for 60 h
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customchromatographed on silicon gel
  5. concentrationThe eluate was concentrated by rotary evaporation

出典と根拠

ORDレコード
ord-97fa9d6e82174653af6734456fc5a3c3
出典データセット
uspto-grants-2001_09
特許番号
US06291722B1

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