Methyl iodide → methyl 3-bromo-5-fluoro-2-methylbenzoate

HRID 1809468노트

반응식

HRID 1809468 반응식
[C:1]([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([OH:13])=[O:12].IC>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([O:13][CH3:1])=[O:12]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666439353-bromo-5-fluoro-2-methylbenzoic acid

생성물 1

HCID 68633230methyl 3-bromo-5-fluoro-2-methylbenzoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

K2CO3 (1.2 eq.) was added to a solution of (E3) in DMF (0.26 M) and the resulting suspension was stirred at RT for 30 min. Then, iodomethane (1.2 eq.) was added and the reaction mixture was stirred at RT overnight. The solution was diluted in EtOAc and the organic phase was washed with brine and dried (Na2SO4). Solvent was removed in vacuo giving a residue that was purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49) yielding (31% over 4 steps) the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 7.74 (1H, dd, J=8.4 and 2.8 Hz), 7.60 (1H, dd, J=7.3 and 2.5 Hz), 3.95 (3H, s), 2.59 (3H, s).

후처리

  1. stirringthe reaction mixture was stirred at RT overnight
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed in vacuo
  5. customgiving a residue that
  6. customwas purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49)

출처 및 근거

ORD 기록
ord-df9a953acf33455baf3f7683c448a36a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362030B2

반응 노트

불러오는 중…