Dimethylformamide → Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

HRID 1295921ノート

反応式

HRID 1295921 の反応式
[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13](=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20].CN(C)[CH:24]=[O:25]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([O:25][CH2:24][CH3:13])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][CH3:20])=[O:8]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2439345-bromo-2-hydroxy-4-methylbenzoic acid

生成物 1

HCID 22929763Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

After dissolving 5-bromo-2-hydroxy-4-methylbenzoic acid (9.35 g) in dimethylformamide, potassium carbonate (14 g) and ethyl iodide (8 ml) were added in that order and the mixture was stirred at 50° C. for 3 hours. It was then diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to yield ethyl 5-bromo-2-ethoxy-4-methylbenzoate. The product was dissolved in ethanol (100 ml), 5 N sodium hydroxide (20 ml) was added and the mixture was heated to reflux for 30 minutes. After adding 5 N hydrochloric acid (25 ml) for neutralization, extraction was performed with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (10.4 g) as a white solid.

後処理

  1. additionwere added in that order
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a77b0601025942b6bf398b731656b7d4
出典データセット
uspto-grants-2007_07
特許番号
US07244730B2

反応ノート

読み込み中…