Iodoethane → Ethyl 4-bromo-3-ethoxybenzoate

HRID 2102892ノート

反応式

HRID 2102892 の反応式
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

生成物 1

HCID 57804236Ethyl 4-bromo-3-ethoxybenzoate収率 62.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Ethyl 4-bromo-3-hydroxybenzoate (prepared according to M. I. Dawson et al WO 2003048101; 0.5 g, 2.04 mmol), potassium carbonate (0.84 g, 6.12 mmol) and iodoethane (0.2 mL, 2.45 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under vacuum to an oil. The oil was purified by column chromatography using EtOAc/hexane (0-50%) as eluent to give the product (0.35 g, 62%) as a clear oil.

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under vacuum to an oil
  8. customThe oil was purified by column chromatography

出典と根拠

ORDレコード
ord-1b5892d5f81848ef9f58b40d43333966
出典データセット
uspto-grants-2009_08
特許番号
US07576099B2

反応ノート

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