Cesium carbonate → HCID 86697028, 화합물

HRID 536175노트

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HRID 536175 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([C:10]([F:13])([F:12])[F:11])[CH:4]=1.[B-](F)(F)(F)[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>COC1CCCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)=[CH:4][C:5]=1[C:10]([F:13])([F:12])[F:11]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 27781144-Chloro-3-(trifluoromethyl)benzyl bromideHCID 23697319Potassium 4-formylphenyltrifluoroborate

생성물 1

HCID 86697028HCID 86697028, 화합물수율 51.9%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 138539Cyclopentyl methyl ether용매

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온도
80 °C

실험 절차

To a suspension of 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene (4.5 g, 16.45 mmol), potassium trifluoro(4-formylphenyl)borate (3.52 g, 16.62 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.672 g, 0.823 mmol) and Cs2CO3 (16.08 g, 49.4 mmol) in cyclopentyl methyl ether (100 mL) and water (100 mL). The mixture was charged with Argon and stirred for overnight at 80° C. The result mixture was cooled to room temperature and partitioned with water 100 mL and ethyl acetate 100 mL. The organic phase was washed by water, brine and dried over sodium sulfate, the solvent was removed and the residue was purified via flash column chromatography. Removed the solvent afforded the title compound (2.55 g). LC-MS (ESI): m/z 299 [M+H]+

후처리

  1. additionThe mixture was charged with Argon
  2. temperatureThe result mixture was cooled to room temperature
  3. custompartitioned with water 100 mL and ethyl acetate 100 mL
  4. washThe organic phase was washed by water, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified via flash column chromatography
  8. customRemoved the solvent

출처 및 근거

ORD 기록
ord-881d5b2c67b74d76915324d994e800fa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859573B2

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