O-Cresol → HCID 67076683、化合物

HRID 521501

反応式

HRID 521501 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH3:14])[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:19]([OH:21])=[O:20]>CN(C=O)C.[Cu]>[CH3:26][O:25][C:24]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[O:13][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:14]

参加物

6

反応物 3

HCID 335O-Cresol2 回HCID 11430Potassium Carbonate2 回HCID 668363-Bromo-4-methoxybenzoic acid

生成物 1

HCID 67076683HCID 67076683、化合物収率 53.7%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
165 °C

実験手順

Potassium carbonate (1.20 g, 8.66 mmol), o-cresol (468 mg, 4.33 mmol), copper powder (28 mg, 0.43 mmol) and 3-bromo-4-methoxybenzoic acid (1.00 g, 4.33 mmol) were suspended in DMF (5 ml) and heated to 165° C. overnight. Potassium carbonate (1.20 g, 8.66 mmol) and o-cresol (468 mg, 4.33 mmol) were added once again and heating was continued for another 2 h. The crude mixture was partitioned between EA and 2 N hydrochloric acid, the aqueous phase extracted with EA, and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield 600 mg of the title compound.

後処理

  1. temperatureheating
  2. customThe crude mixture was partitioned between EA and 2 N hydrochloric acid
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

出典と根拠

ORDレコード
ord-013c62593d8d4919bc487603c80ca7a4
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

関連ノート

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