Sodium Carbonate → HCID 68900889, 화합물

HRID 735305노트

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HRID 735305 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O.COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][C:18]=3[F:20])[CH:3]=2)[CH:8]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 6405912,6-DibromonaphthaleneHCID 27343342,4-Difluorophenylboronic acid

생성물 1

HCID 68900889HCID 68900889, 화합물수율 17.8%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A mixture of 2,6-dibromonaphthalene (12.49 g, 43.7 mmol), 2,4-difluorobenzeneboronic acid (3.44 g, 21.8 mmol), sodium carbonate (4.63 g, 45.7 mmol), palladium acetate (245 mg, 1.09 mmol) and tri-o-tolylphosphine (667 mg, 2.19 mmol) in water (15 mL) and ethylene glycol dimethyl ether (90 mL) was degassed and heated to 80° C. overnight. The cooled reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with isohexane, to give 2-bromo-6-(2,4-difluorophenyl)naphthalene (1.24 g, contains 10% 2,6-dibromonaphthalene). 1H NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.93 (1H, s), 7.82 (1H, d, J=8.5 Hz), 7.75 (1H, d, J=8.6 Hz), 7.62 (2H, dd, J=8.4, 31.8 Hz), 7.50 (1H, m), 7.04-6.91 (2H, m).

후처리

  1. customwas degassed
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica
  9. washeluting with isohexane

출처 및 근거

ORD 기록
ord-690cdbc5f5fa402990a4cc7c24bb6239
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592456B2

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