Tetrahydrofuran → 2-(4-Bromo-3,5-dimethoxyphenyl)furan

HRID 56505노트

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HRID 56505 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](I)[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[Br:9].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1COCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:7]=1[O:10][CH3:11]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 584320782-Bromo-5-iodo-1,3-dimethoxybenzene

생성물 1

HCID 584319882-(4-Bromo-3,5-dimethoxyphenyl)furan수율 91.2%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

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온도
60 °C

실험 절차

2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized according to the procedure reported in WO 2008/040669 as follows. To a round bottom flask containing 3,5-dimethoxy-4-bromo-iodobenzene (7.9 g, 85% purity, 19.6 mmol), 2-furylboronic acid (3.4 g, 30.4 mmol), triphenylphosphine (0.358 g, 1.37 mmol), tetrabutylammonium bromide (7.94 g, 14.6 mmol) and Na2CO3 (4.9 g, 46.2 mmol) was added THF (87 mL) and H2O (87 mL). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each. 10% Pd/C (1.36 g) was added and the mixture was heated at 60° C. for 17 hrs under argon. After cooling to room temperature, the mixture was filtered through Celite and rinsed with THF and EtOAc. The filtrate layers were separated and the organic layer was washed with brine, dried over Na2SO4 and concentrated. Purification by column chromatography (0-25% Et2O-hexanes) gave 2-(4-bromo-3,5-dimethoxyphenyl)furan as a white solid (5.06 g, 91% yield). Product TLC Rf 0.35 (15% EtOAc-hexanes TLC eluent).

후처리

  1. custom2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized
  2. customThe mixture was degassed
  3. waitby alternately putting under house vacuum and argon three times for several minutes
  4. addition10% Pd/C (1.36 g) was added
  5. temperatureAfter cooling to room temperature
  6. filtrationthe mixture was filtered through Celite
  7. washrinsed with THF and EtOAc
  8. customThe filtrate layers were separated
  9. washthe organic layer was washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customPurification by column chromatography (0-25% Et2O-hexanes)

출처 및 근거

ORD 기록
ord-e5c3108e24c24884b9b775958aab502d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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