Trifluoroacetic acid → 5-Bromo-2-isopropylbenzaldehyde

HRID 72626노트

반응식

HRID 72626 반응식
FC(F)(F)C(O)=O.[CH:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])([CH3:10])[CH3:9].[Br:19]NC(=O)CCC(N)=O>S(=O)(=O)(O)O>[Br:19][C:16]1[CH:17]=[CH:18][C:11]([CH:8]([CH3:10])[CH3:9])=[C:12]([CH:15]=1)[CH:13]=[O:14]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 5905362-(Propan-2-yl)benzaldehydeHCID 9834204N-Bromosuccinamide

생성물 1

HCID 583408355-Bromo-2-isopropylbenzaldehyde수율 58.7%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

To a solution of trifluoroacetic acid (50 ml) and 2-isopropylbenzaldehyde (2.0 g, 13.5 mmol) was added conc. sulphuric acid (98%) (10 ml) at room temperature, followed by N-bromosuccinamide (NBS, 3.6 g 20.2 mmol) in portions. After 2 hrs, the mixture was poured into ice water and extracted with dichloromethane (3×30 mL). The organic layers were combined and neutralized with saturated aqueous sodium bicarbonate, washed with brine (30 mL), dried over sodium sulfate and concentrated. The resulting residue was purified by column chromatography to furnish 5-bromo-2-isopropylbenzaldehyde (1.80 g).

후처리

  1. extractionextracted with dichloromethane (3×30 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-ee557a7feafe40a1af75b03740360b77
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828951B2

반응 노트

불러오는 중…