Sodium Carbonate → 2-Bromo-4'-chloro-1,1'-biphenyl

HRID 1476263노트

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HRID 1476263 반응식
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.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>[Br:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 114141,2-DibromobenzeneHCID 742994-Chlorophenylboronic acid

생성물 1

HCID 129394052-Bromo-4'-chloro-1,1'-biphenyl수율 71%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

Sodium carbonate (19.8 g, 186.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.90 mmol) were added to a solution of 1,2-dibromobenzene (12.8 ml, 105.98 mmol) and 4-chlorophenylboronic acid (14.1 g, 90.08 mmol) in toluene (170 ml) and water (80 ml). The mixture was purged with nitrogen and heated at reflux overnight. The reaction mixture was allowed to cool to room temperature, and partitioned between saturated aq. NH4Cl and ethyl acetate (500 ml). The organic layer was dried over MgSO4, filtered and the volatiles were evaporated under reduced pressure to give a residue. The residue was purified by column chromatography (ISCO, 330 g silica gel column, eluting with 100% hexanes) to give the title product (17.0 g, yield: 71%).

후처리

  1. customThe mixture was purged with nitrogen
  2. temperatureheated
  3. temperatureat reflux overnight
  4. custompartitioned between saturated aq. NH4Cl and ethyl acetate (500 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe volatiles were evaporated under reduced pressure
  8. customto give a residue
  9. customThe residue was purified by column chromatography (ISCO, 330 g silica gel column, eluting with 100% hexanes)

출처 및 근거

ORD 기록
ord-1aa927c2431c4c5e9633d685c2441042
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018381B2

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