Hexane → 2',4',6'-Trimethyl-3-nitro-biphenyl-2-carboxylic acid methyl ester

HRID 377045

反応式

HRID 377045 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4](OC)=O.[F-].[Cs+].[C:17]1([CH3:28])[CH:22]=[C:21](C)[CH:20]=[C:19]([CH3:24])[C:18]=1B(O)O.CCCCCC.[C:35]([O:38][CH2:39]C)(=[O:37])C>C(COC)OC.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>[CH3:39][O:38][C:35]([C:8]1[C:3]([C:4]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:24])=[CH:18][C:17]=2[CH3:28])=[CH:2][CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13])=[O:37]

参加物

8

反応物 5

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 2921842,4,6-Trimethylbenzeneboronic acid

生成物 1

HCID 538563352',4',6'-Trimethyl-3-nitro-biphenyl-2-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Under a nitrogen atmosphere in 20 ml of anhydrous dimethoxyethane (DME) was combined 1.44 g (5.54 mmol) of methyl 2-bromo-5-nitrobenzoate 1.68 g (11.1 mmol) of cesium fluoride and 192 mg of tetrakis(triphenylphosphine)palladium(0). The reaction was stirred for 5 minutes, at which point 1.00 g (6.09) of mesitylboronic acid was added. The solution was heated to reflux for 20 hours, and was then cooled and fractionated on silica gel using 6:1 hexane: ethyl acetate (EtOAc) to afford, after concentration in vacuo and refractionation using toluene, 5.65 g (54%) of the title compound.

後処理

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for 20 hours
  4. temperaturewas then cooled
  5. concentrationafter concentration in vacuo and refractionation

出典と根拠

ORDレコード
ord-43ad98a996a64243884dad4eee8f09b5
出典データセット
uspto-grants-2000_02
特許番号
US06022978

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