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

HRID 1809468ノート

反応式

HRID 1809468 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-df9a953acf33455baf3f7683c448a36a
出典データセット
uspto-grants-2013_01
特許番号
US08362030B2

反応ノート

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