Sodium Hydroxide → 3-Iodo-5-(trifluoromethyl)benzaldehyde

HRID 217502

반응식

HRID 217502 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)[CH:12]=[O:13]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 192615723-Iodo-5-(trifluoromethyl)benzyl alcohol

생성물 1

HCID 534147093-Iodo-5-(trifluoromethyl)benzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [3-iodo-5-(trifluoromethyl)phenyl]methanol (287 mg, 0.95 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and then Dess-Martin periodinane (604 mg, 1.42 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 10% EtOAc/hexanes afforded 3-iodo-5-(trifluoromethypbenzaldehyde. Rf=0.54 (15% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 9.98 (s, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H).

후처리

  1. extractionThe mixture was extracted with EtOAc (50 mL)
  2. washthe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 0% to 10% EtOAc/hexanes
  7. customafforded 3-iodo-5-(trifluoromethypbenzaldehyde

출처 및 근거

ORD 기록
ord-3ff2b1f71e1e4df9b60fabb2eb55bc9e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193365B2

연결된 노트

불러오는 중…