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

HRID 1295921노트

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HRID 1295921 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a77b0601025942b6bf398b731656b7d4
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244730B2

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