Cesium carbonate → HCID 86697028、化合物

HRID 536175ノート

反応式

HRID 536175 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 86697028HCID 86697028、化合物収率 51.9%

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 138539Cyclopentyl methyl ether溶媒

反応条件

温度
80 °C

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-881d5b2c67b74d76915324d994e800fa
出典データセット
uspto-grants-2014_10
特許番号
US08859573B2

反応ノート

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