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

HRID 1267108ノート

反応式

HRID 1267108 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 185454465'-Chloro-2'-methyl4-trifluoromethyl-biphenyl収率 93.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5008ef1b3ea04cb88930c85a9ab56e0f
出典データセット
uspto-grants-2003_04
特許番号
US06552022B1

反応ノート

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