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Sodium Carbonate → 2-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrile

HRID 1178535
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HRID 1178535 반응식
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH:21]=[O:22])[O:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].C1(B(O)O)C=CC=CC=1.[C:32](=O)([O-])[O-:33].[Na+].[Na+]>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(O)C>[CH:21]([C:20]1[CH:19]=[CH:18][C:4]([O:5][C:6]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=2[C:8]#[N:9])=[C:3]([O:33][CH3:32])[CH:2]=1)=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 219303412-(3-Bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

생성물 1

HCID 219304562-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrile수율 14%

시약·촉매·용매 4

HCID 178506421HCID 178506421, 화합물촉매
HCID 702
Ethanol
용매
HCID 962Water용매2회
HCID 80711,2-Dimethoxyethane용매

실험 절차

Under nitrogen, 2-(3-bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (0.87 g, 2.6 mmol), phenylboronic acid (336 mg, 2.7 mmol), 1,1′-bis(diphenyl)phosphino-ferrocene palladium (9 mg, 0.13 mmol) and sodium carbonate (331 mg, 3.1 mmol) in dimethoxyethane:water:ethanol solution (7:3:2, 10 mL) was stirred at 60° C. for 6 h and then at 40° C. for 16 h. The mixture was then poured over water, extracted into ethyl acetate, and dried over MgSO4. The crude material was chromatographed on an ISCO CombiFlash Chromatography System to yield 2-(4-formyl-2-methoxy-phenoxy)-4-trifluoromethyl-benzonitrile as a clear oil (117 mg, 14%).

후처리

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over MgSO4
  3. customThe crude material was chromatographed on an ISCO CombiFlash Chromatography System

출처 및 근거

ORD 기록
ord-d35b9e39d2ce4c00ba82e751e24b9cf3
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07276528B2

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