Hydrochloric Acid → 2-Iodo-5-(trifluoromethyl)benzaldehyde

HRID 1994521노트

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HRID 1994521 반응식
[I:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#N.CC(C[AlH]CC(C)C)C.Cl.CC[O:26]CC>C(Cl)Cl>[I:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:26]

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydride2회HCID 533636442-Iodo-5-(trifluoromethyl)benzonitrile

생성물 1

HCID 716509062-Iodo-5-(trifluoromethyl)benzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 2-iodo-5-(trifluoromethyl)benzonitrile (EXAMPLE 2, 42 g) in CH2Cl2 (300 mL) at −78° C. was added a solution of DIBAL in CH2Cl2 (175 mL, 1M) over 30 minutes. A precipitate formed. The reaction was warmed to 0° C. An additional 25 mL of the DIBAL solution was added dropwise over 30 minutes. The reaction was poured into 200 mL 2N aqueous HCl, diluted with ether and stirred 1 hour. TLC analysis indicates imine still present and an additional 100 mL 2N aqueous was added and the reaction stirred overnight. Imine was still present by TLC analysis and 200 mL 2N aqueous HCl was added and the mixture stirred 2 hours. The layers were separated and the aqueous layer back extracted with ether. The ether extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel chromatography eluting with 95:5 hexanes/EtOAc to give 2-Iodo-5-(trifluoromethyl)benzaldehyde as a white solid. 1H NMR (500 MHz, CDCl3): δ 10.00 (s, 1H), 8.12 (s, 1H), 8.11 (d, J=8 Hz, 1H), 7.53 (dd, J=2 Hz, 8 Hz, 1H).

후처리

  1. customA precipitate formed
  2. additionan additional 100 mL 2N aqueous was added
  3. stirringthe reaction stirred overnight
  4. additionwas added
  5. stirringthe mixture stirred 2 hours
  6. customThe layers were separated
  7. extractionthe aqueous layer back extracted with ether
  8. washwashed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was purified by silica gel chromatography
  13. washeluting with 95:5 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-bffa277419db474fb4ad236cc8da4217
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652049B2

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