4-Bromoanisole → 1-(5-Bromo-2-hydroxyphenyl)-2-o-tolylethanone

HRID 239610

반응식

HRID 239610 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.CN(C=O)C>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[C:23]([C:9](=[O:11])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH:24]=1

참가 물질

7

반응물 4

HCID 77304-BromoanisoleHCID 65578Oxalyl chlorideHCID 69519o-Tolylacetic acidHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 532343631-(5-Bromo-2-hydroxyphenyl)-2-o-tolylethanone수율 33%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

2-Methylphenylacetic acid (9.60 g, 64.15 mmoles) was dissolved in 10 ml dichloromethane. To this mixture, oxalylchloride (7 ml, 80.19 mmoles) and DMF (3 drops) were added at 0° C. and stirred for 30 min. The solvent was evaporated and dissolved in 100 ml dichloromethane. To this mixture, 4-bromoanisole (10 g, 53.47 mmoles) was added and cooled to 0° C. At 0° C. AlCl3 (10.6 g, 80.19 mmoles) was added and the reaction mixture was warmed to RT and stirred for 24 h. The reaction mixture was quenched by the addition of 2N HCl and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as white solid (5.5 g, 33% yield. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 11.52(s,1H), 8.02(d, J=2.4 Hz, 1H), 7.65(dd, J=8.8, 2.5 Hz, 1H), 7.16(m, 4H), 6.97(d, J=8.9 Hz, 1H), 4.47(s, 2H), 2.14(s, 3H).

후처리

  1. customThe solvent was evaporated
  2. dissolutiondissolved in 100 ml dichloromethane
  3. customAt 0° C
  4. temperaturethe reaction mixture was warmed to RT
  5. stirringstirred for 24 h
  6. customThe reaction mixture was quenched by the addition of 2N HCl
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography with ethyl acetate

출처 및 근거

ORD 기록
ord-7584a19b4fdd4b498a1059ad21bb3e7e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642607B2

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