Sodium Carbonate → 5'-Chloro-2'-methyl4-trifluoromethyl-biphenyl

HRID 1267108

반응식

HRID 1267108 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[Na+].[Na+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.CO.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>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 6098982-Bromo-4-chloro-1-methylbenzeneHCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 185454465'-Chloro-2'-methyl4-trifluoromethyl-biphenyl수율 93.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

To a solution of 2-bromo-4-chloro-toluene (20.5 g) in toluene (100 mL) was added Pd(PPh3)4 (1 g) and the mixture was stirred at room temperature under N2 for 0.25 hours. A 2M solution of Na2CO3 (100 mL) was then added, followed by the dropwise addition of 4-trifluoromethylphenyl boronic acid (19 g) in MeOH (100 mL). The resulting mixture was heated under reflux for 48 hours. The mixture was then cooled to room temperature and the phases were separated. The organic layer was then dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with petroleum ether/AcOEt (90/10) to give the title compound (25.3 g) as a colorless liquid.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 48 hours
  3. temperatureThe mixture was then cooled to room temperature
  4. customthe phases were separated
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography
  9. washeluting with petroleum ether/AcOEt (90/10)

출처 및 근거

ORD 기록
ord-5008ef1b3ea04cb88930c85a9ab56e0f
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552022B1

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