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Toluene → Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate

HRID 402828
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HRID 402828 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[CH:24]1([B-](F)(F)F)[CH2:26][CH2:25]1.[K+].[C:32]1([CH3:38])C=CC=C[CH:33]=1>O.CC([O-])=O.CC([O-])=O.[Pd+2].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2>[CH:24]1([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([CH:38]3[CH2:32][CH2:33]3)[C:11]=2[O:12][C:13]([F:16])([F:15])[F:14])[C:5]([O:7][CH3:8])=[O:6])[CH2:26][CH2:25]1
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8

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HCID 1140TolueneHCID 10796Cesium carbonateHCID 23697338Potassium cyclopropyltrifluoroborateHCID 66764920Methyl 3,5-dibromo-4-(trifluoromethoxy)benzoate

생성물 1

HCID 66764880Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 11371790Bis(adamantan-1-yl)(butyl)phosphane촉매
HCID 962Water용매2회

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온도
100 °C

실험 절차

To methyl 3,5-dibromo-4-(trifluoromethoxy)benzoate (500 mg, 1.32 mmol), Cs2CO3 (2586 mg, 7.94 mmol), Pd(OAc)2 (11.9 mg, 0.053 mmol), potassium cyclopropyltrifluoroborate (470 mg, 3.18 mmol) and di(1-adamantyl)-n-butylphosphine (28.5 mg, 0.079 mmol) was added toluene (12 mL) and water (1.2 mL). The reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled to room temperature, diluted with water, extracted with DCM and evaporated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes) to yield the title compound (259 mg).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with DCM
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (0-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-7fd07df0264a410eac9a56bdedf98093
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08742110B2

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