3-Methoxytoluene → (4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone

HRID 229148

반응식

HRID 229148 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[CH:16]=[CH:15][C:14]([O:18][CH3:19])=[CH:13][C:12]=2[CH3:11])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 75303-MethoxytolueneHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 11023132(4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone수율 73%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 4-bromobenzoyl chloride (1.12 g, 5.12 mmol) and 3-methyl anisole (1.95 mL, 15.47 mmol) at 0° C. was added AlCl3 (0.83 g, 6.20 mmol). The mixture was allowed to warm to RT over 12 h with stirring. Water was added slowly, and the mixture was extracted with CH2Cl2. The organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography on silica gel (EtOAc:hexanes) to yield 1.14 g (73%) of compound 27. 1H NMR (400 MHz, CDCl3): δ 2.41 (s, 3H), 3.86 (s, 3H), 6.74 (dd, J=2.5 Hz, 8.6 Hz, 1H), 6.82 (d, J=2.6 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H).

후처리

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organics were dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by chromatography on silica gel (EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-c25237681b384baa81e76366647fb27b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560589B2

연결된 노트

불러오는 중…