Hydrochloric Acid → 3,5-Diethyl-1-bromobenzene

HRID 478588

反応式

HRID 478588 の反応式
[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5](N)=[C:4]([CH2:11][CH3:12])[CH:3]=1.Cl.N([O-])=O.[Na+].O[PH2]=O>O.CCO.C(O)(=O)C>[CH2:11]([C:4]1[CH:3]=[C:2]([Br:1])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:5]=1)[CH3:12]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6114524-Bromo-2,6-diethylanilineHCID 4124402Phosphinic AcidHCID 23668193Sodium Nitrite

生成物 1

HCID 119590293,5-Diethyl-1-bromobenzene収率 96.3%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
-5 °C

実験手順

A mixture of 20 g of 4-bromo-2,6-diethylaniline, 160 ml of acetic acid, 100 ml of concentrated HCl solution, 30 ml of water and 100 ml of EtOH is cooled to −5° C., a solution of 6.6 g of sodium nitrite in 25 ml of water is added dropwise and the mixture is left stirring at RT for 30 minutes. The reaction mixture is poured into 170 ml of 50% H3PO2 cooled to 0° C. and is left stirring for 2 hours at 0° C. and then for 48 hours at RT. The reaction mixture is extracted with ether, the organic phase is washed with water, with 1N NaOH solution, with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with cyclohexane. 18 g of the expected product are obtained.

後処理

  1. waitthe mixture is left
  2. temperaturecooled to 0° C.
  3. waitis left
  4. stirringstirring for 2 hours at 0° C.
  5. waitfor 48 hours at RT
  6. extractionThe reaction mixture is extracted with ether
  7. washthe organic phase is washed with water, with 1N NaOH solution, with water
  8. dry with materialdried over Na2SO4
  9. customthe solvent is evaporated off under vacuum
  10. customThe residue is chromatographed on silica gel
  11. washeluting with cyclohexane

出典と根拠

ORDレコード
ord-9027dcd0ed55406e92ef7b8714859fbb
出典データセット
uspto-grants-2003_11
特許番号
US06642233B1

関連ノート

読み込み中…