Methyl Ethyl Ketone → 1,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

HRID 399010ノート

反応式

HRID 399010 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][Cl:20].CC(=O)CC>C(OCC)C>[Cl:20][CH2:19][CH2:18][O:10][C:3]1[C:2]([Br:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[Br:9]

参加物

6

反応物 4

HCID 6569Methyl Ethyl KetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 676542,6-Dibromo-4-fluorophenol

生成物 1

HCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene収率 99.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 2,6-dibromo-4-fluoro-phenol (55 g, 0.20 mol), potassium carbonate (60 g, 0.43 mol), 1-bromo-2-chloroethane (32.5 g, 0.23 mol) and 2-butanone (500 mL) was heated to reflux for 2 hours and allowed to cool to ambient temperature. The solids were filtered and the solvent was removed under vacuum to afford an oil. The oil was dissolved in diethyl ether (300 mL) and washed with water, dried over anhydrous magnesium sulfate, charcoalized, and filtered through Solka floc to afford 65.9 g (97.2%) of an oil; MS EI m/e 330/332/334/336 (M+ ; 1H NMR (CDCl3) δ 3.89 (2H, t, J=6.1 Hz), 4.23 (2H, t, J=6.1 Hz), 7.28 (2H, d, J=7.5 Hz).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe solids were filtered
  4. customthe solvent was removed under vacuum
  5. customto afford an oil
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered through Solka floc

出典と根拠

ORDレコード
ord-1a72ba867804443a92f5ceca73991469
出典データセット
uspto-grants-1998_10
特許番号
US05817690

反応ノート

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