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

HRID 1884185

反応式

HRID 1884185 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+]>O1CCOCC1.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].N(P(Cl)Cl)(C1CCCCC1)C1CCCCC1>[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

7

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 99.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 13311825HCID 13311825、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

The general procedure from Example 12 was followed using 4-chloroanisole (143 mg, 1.0 mmol) and 4—MeOC6H4B(OH)2 (228 mg, 1.5 mmol) with Pd2(dba)3 (13.3 mg, 0.0145 mmol) and (Me3C)2PH(O) from Experiment 2 (9.6 mg, 0.058 mmol) and CsF (456 mg, 3.0 mmol) in 3.0 mL of 1,4-dioxane. After 24 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 213 mg (99% yield) of 4-(4-methoxyphenyl)anisole. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.38 (d, J=8.68 Hz, 4H), 6.86 (d, J=8.68 Hz, 4H), 3.74 (s, 6H) ppm. 13C NMR (125 MHz, CDCl3): δ158.7, 133.5, 127.7, 114.2, 55.3 ppm.

後処理

  1. customthe reaction mixture was chromatographed with 5% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-2503825783664ca3af87338fb6ef19e2
出典データセット
uspto-grants-2004_07
特許番号
US06762330B2

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