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2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → Tert-butyl 2-(2-chloro-4-cyanophenyl)acetate

HRID 526433
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HRID 526433 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:10].[Cl-].[C:12]([O:16][C:17](=[O:20])[CH2:18][Zn+])([CH3:15])([CH3:14])[CH3:13].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:10][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20]
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6

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HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 166593954-Bromo-3-chlorobenzonitrileHCID 178451183HCID 178451183, 화합물

생성물 1

HCID 117601114Tert-butyl 2-(2-chloro-4-cyanophenyl)acetate수율 39.3%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

Combined 4-bromo-3-chlorobenzonitrile (0.600 g, 2.77 mmol) and (2-(tert-butoxy)-2-oxoethyl)zinc(II) chloride (8.32 mL, 4.16 mmol) in THF (5.54 mL), then Pd(dba)2 (0.080 g, 0.139 mmol) and 2′-(dicyclohexylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine (0.109 g, 0.277 mmol) were added and the reaction was refluxed overnight at 65° C. The reaction was concentrated by rotary evaporation and purified on a silica gel column eluting with hexanes and EtOAc to give the title compound (274 mg, 39%) as a yellow oil. MS m/z [M+H]+ 252.

후처리

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. custompurified on a silica gel column
  3. washeluting with hexanes and EtOAc

출처 및 근거

ORD 기록
ord-d0e9cd12f12e435d9c8167f240aaa764
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09345713B2

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