Hydrochloric Acid → 2-Fluoro-4-(naphthalen-2-yl)benzaldehyde

HRID 1712197

반응식

HRID 1712197 반응식
C([Li])(CC)C.[F:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[CH:10]=[CH:11][CH:12]=1.[CH:23](N1CCOCC1)=[O:24].Cl>C1COCC1.C1CCCCC1>[F:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)[CH:10]=[CH:11][C:12]=1[CH:23]=[O:24]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 20417N-FormylmorpholineHCID 542381022-(3-Fluorophenyl)naphthaleneHCID 178418400CID 53628100

생성물 1

HCID 549124512-Fluoro-4-(naphthalen-2-yl)benzaldehyde수율 59.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

실험 절차

A 86.86 ml cyclohexane solution of sec-butyl lithium in a concentration of 1.01M was dropped into a 300 ml THF solution of 15.00 g (=67.49 mmol) of 2-(3-fluorophenyl)naphthalene at −70° C. After the dropping was finished, the reaction solution was stirred at the same temperature for 1 hour, added with a 150 ml THF solution of 10.88 g (=94.49 mmol) of 4-formylmorpholine through dropping and then slowly heated to room temperature. After being stirred for 18 hours, 25 ml of 6N HCl(aq) was dropped into the reaction solution, and then the reaction mixture was extracted thrice with toluene. The extract was washed with water and an aqueous solution of NaHCO3, and then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained yellow solid of 16.83 g was purified with silica gel chromatography using toluene as the eluent to obtain a yellowish solid of 13.26 g, which was further recrystallized with toluene to obtain 10.09 g of 2-fluoro-4-naphthalene-2-yl-benzaldehyde as yellowish crystals.

후처리

  1. stirringAfter being stirred for 18 hours
  2. extractionthe reaction mixture was extracted thrice with toluene
  3. washThe extract was washed with water
  4. dry with materialan aqueous solution of NaHCO3, and then dried with anhydrous MgSO4
  5. customAfter the solvent was evaporated under a reduced pressure
  6. customthe obtained yellow solid of 16.83 g was purified with silica gel chromatography
  7. customto obtain a yellowish solid of 13.26 g, which
  8. customwas further recrystallized with toluene

출처 및 근거

ORD 기록
ord-6fa4cf8be31045d09e1498835abfe99d
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790915B2

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