Potassium Phosphate, Tribasic → 1,8-Bis(2'-methyl-4'-methoxyphenyl)naphthalene

HRID 1525747ノート

反応式

HRID 1525747 の反応式
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2I)[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[CH3:13])[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 6332861,8-DiiodonaphthaleneHCID 2773486(4-Methoxy-2-methylphenyl)boronic acid

生成物 1

HCID 708193991,8-Bis(2'-methyl-4'-methoxyphenyl)naphthalene収率 99%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A solution of 1,8-diiodonaphthalene, (1.70 g, 4.5 mmol), 2-methyl-4-methoxyphenylboronic acid, 2, (2.20 g, 13.4 mmol), Pd(PPh3)4 (0.78 g, 0.67 mmol) and K3PO4, (4.30 g, 20.1 mmol) in 50 mL toluene was stirred at 100° C. for 18 hours. The resulting mixture was allowed to come to room temperature, quenched with water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2Cl2:hexanes 2:3) afforded 1.65 g (4.5 mmol, >99%) of off-white crystals containing syn- and anti-isomers of 7 in a ratio of 1:3.

後処理

  1. customto come to room temperature
  2. customquenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (CH2Cl2:hexanes 2:3)

出典と根拠

ORDレコード
ord-c2f4bed70b264e1cb64b9e60b8139a70
出典データセット
uspto-grants-2015_07
特許番号
US09085511B2

反応ノート

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