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Sodium Carbonate → HCID 12085902, 화합물

HRID 1860293
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HRID 1860293 반응식
Br/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[C:3](\[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)/[CH2:4][CH3:5].[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([C:21]1[CH:26]=[CH:25][C:24](/[C:2](/[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:3](\[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)/[CH2:4][CH3:5])=[CH:23][CH:22]=1)=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 12085901HCID 12085901, 화합물

생성물 1

HCID 12085902HCID 12085902, 화합물수율 92.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

To a solution of the bromide 3 (2.0 g, 6.54 mmol) in DME (30 mL) was added 4-formylbenzene boronic acid (1.37 g, 9.11 mmol), tetrakis(triphenylphosphine)palladium(0) (800 mg, 0.7 mmol), and 2N aqueous sodium carbonate(4.8 mL, 9.6 mmol). After refluxing overnight the solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 5% EtOAc/hexanes) to give the aldehyde (4) as a white solid (2.0 g, 92%): 1 H NMR (CDCl3) δ 9.83 (m, 1 H), 7.52 (d, J=8.4 Hz, 2 H), 7.15 (m, 11 H), 2.49 (q, J=7.3 Hz, 2 H), 0.94 (t, J=7.3 Hz, 3 H); APcI m/z: 372 (M+H+CH3CN+, 100%).

후처리

  1. temperatureAfter refluxing overnight the solvent
  2. customwas removed under reduced pressure
  3. customthe residue was chromatographed (silica gel, 5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b31e0ba5113a41208d3ecf0769d6384d
출처 데이터셋
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06528681B2

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