2-Bromo-6-nitrotoluene → 1-Mesityl-2-methyl-1-nitrobenzene

HRID 584813

反応式

HRID 584813 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[C:12]1([CH3:24])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.O.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>[C:12]1([CH3:24])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[C:4]1([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]1[CH3:11]

参加物

7

反応物 3

HCID 1235372-Bromo-6-nitrotolueneHCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acid

生成物 1

HCID 223413561-Mesityl-2-methyl-1-nitrobenzene収率 92.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 107951,1-Dimethoxyethane溶媒

実験手順

A solution of 2-bromo-6-nitrotoluene (10.0 g, 46 mmol), mesitylboric acid (8.3 g, 51 mmol), Pd(PPh3)4 (2.7 g, 2.31 mmol) and barium hydroxide octahydrate (21.9 g, 69 mmol) in 2,2-dimethoxyethane (300 mL) and water (50 mL) was heated under reflux for six hours. The mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (0-1% ethyl acetate/hexane), to give the title compound (11.0 g) as white crystals.

後処理

  1. temperatureunder reflux for six hours
  2. filtrationThe mixture was filtered through Celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (0-1% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-1ab0d644cd03436a84a1519a8e6ea98d
出典データセット
uspto-grants-2005_08
特許番号
US06927221B2

関連ノート

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