Water → 4-Bromo-2-(trifluoromethyl)benzaldehyde

HRID 415998ノート

反応式

HRID 415998 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Br)Br)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C1C[O:18]CC1.O>[N+]([O-])([O-])=O.[Ag+].C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:18])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

参加物

6

反応物 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59474514Benzene, 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)-

生成物 1

HCID 121872184-Bromo-2-(trifluoromethyl)benzaldehyde収率 81%

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 8857Ethyl Acetate溶媒

実験手順

Combine 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)benzene (6.66 g, 16.8 mmol), silver nitrate (14.8 g, 87.3 mmol), THF (250 mL), and water (35 mL) in a 500 mL flask equipped with a magnetic stir bar, reflux condenser, and N2 inlet. Reflux the mixture while stirring for 2.5 hours then cool to room temperature. Filter the reaction through Celite®, add ethyl acetate (250 mL) and wash with water (2×200 mL) then saturated aqueous sodium chloride solution (1×200 mL). Dry over anhydrous magnesium sulfate, concentrate to an orange oil, and purify the crude product via silica gel chromatography eluting with hexanes to afford 3.46 g (81%) of the product as a clear oil: 1H NMR (300 MHz, CDCl3) δ 10.35-10.33 (m, 1H), 8.0 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=1.4 Hz), 7.86 (dd, 1H, J=1.2 Hz, J=8.3 Hz).

後処理

  1. temperaturereflux condenser, and N2 inlet
  2. temperatureReflux the mixture
  3. filtrationFilter
  4. customthe reaction through Celite®
  5. washwash with water (2×200 mL)
  6. dry with materialDry over anhydrous magnesium sulfate
  7. concentrationconcentrate to an orange oil
  8. custompurify the crude product via silica gel chromatography
  9. washeluting with hexanes

出典と根拠

ORDレコード
ord-4ce2748c2c844cc4a61beb76d4189b03
出典データセット
uspto-grants-2012_01
特許番号
US08088776B2

反応ノート

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