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Diisopropylamine → 2-Bromo-6-fluorobenzaldehyde

HRID 15400
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HRID 15400 반응식
C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:15]=[C:16]([F:20])[CH:17]=[CH:18][CH:19]=1.[Cl-].[NH4+].[O:23]1CCC[CH2:24]1>O.CN(C)C=O>[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[CH:24]=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 140821-Bromo-3-fluorobenzeneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

생성물 1

HCID 224739772-Bromo-6-fluorobenzaldehyde

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of diisopropylamine (2.65 mL) in tetrahydrofuran (30 mL) was added n-butyllithium (2.44 mol/L n-hexane solution, 7.03 mL) at −78° C. under an argon atmosphere, and the mixture was stirred at the same temperature for 5 minutes. To the reaction mixture was added 3-bromofluorobenzene (3 g), and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added N,N-dimethylformamide (1.45 mL), and the mixture was stirred at the same temperature for 10 minutes, then a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was stirred under ice-cooling for 5 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The extract washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give the title compound (3.43 g).

후처리

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringthe mixture was stirred at the same temperature for 10 minutes
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 5 minutes
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-9b32939980df43e6b1eb49e473bef3e4
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07732596B2

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