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

HRID 377045

반응식

HRID 377045 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-43ad98a996a64243884dad4eee8f09b5
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022978

연결된 노트

불러오는 중…