(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol → 4'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde

HRID 1043437노트

반응식

HRID 1043437 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:17]=[O:18])=[CH:10][C:11]([N:14]([CH3:15])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

참가 물질

3

반응물 1

HCID 59266574(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol

생성물 1

HCID 592665494'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde수율 70%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

IBX (3.29 g, 11.76 mmol) was added to a solution of (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.8 g, 5.88 mmol) in dmso (50 mL) and stirred at 40° C. for 3 hours. The reaction was diluted with water and extracted with diethyl ether. The ether layer was dried over MgSO4, filtered and evaporated to give the crude material. The crude product was purified on the Biotage (5-20% EtOAc:Hex) to give 4′-bromo-4-(dimethylamino)biphenyl-2-carbaldehyde (1.25 g, 4.11 mmol, 70% yield) as a yellow solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 2.95-3.13 (m, 6H) 7.01 (dd, J=8.55, 3.05 Hz, 1H) 7.22 (m, 2H) 7.28-7.33 (m, 2H) 7.57 (m, 2H) 9.96 (s, 1H).

후처리

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude material
  6. customThe crude product was purified on the Biotage (5-20% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-4974b1aeb3d0461487574852b37b97d4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563505B2

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