Methanol → 5-Bromo-2-(1-carboxy-ethoxy)-benzoic acid

HRID 402918노트

반응식

HRID 402918 반응식
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH:12]([C:14]([O:16]CC)=[O:15])[CH3:13].CO.[OH-].[Na+]>C1COCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH:12]([C:14]([OH:16])=[O:15])[CH3:13])=[C:4]([CH:9]=1)[C:3]([OH:19])=[O:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 591920375-Bromo-2-(1-ethoxycarbonyl-ethoxy)-benzoic acid methyl ester

생성물 1

HCID 591920275-Bromo-2-(1-carboxy-ethoxy)-benzoic acid수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

A solution of 5-bromo-2-(1-ethoxycarbonyl-ethoxy)-benzoic acid methyl ester (41.1 g, 124 mmol) in a mixture of THF (250 mL), MeOH (250 mL) and a 5 M aqueous NaOH solution (300 mL) is heated under reflux (85° C.) for 16 h. After cooling to room temperature the resulting suspension is concentrated by rotary evaporation. The residue is dissolved in water and acidified with an aqueous concentrated HCl solution under cooling with ice. The aqueous phase is extracted twice with EtOAc and the combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford the title compound as a beige solid (31.5 g, 109 mmol, 88%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=13.04 (bs, 2H), 7.72 (d, J=2.7 Hz, 1H), 7.63 (dd, J=8.9, 2.7 Hz, 1H), 6.92 (d, J=8.9 Hz, 1H), 4.90 (q, J=6.6 Hz, 1H), 1.49 (d, J=6.6 Hz, 3H). MS (ES+): 289 (M(C10H979BrO5)+H)+.

후처리

  1. temperatureAfter cooling to room temperature the resulting suspension
  2. concentrationis concentrated by rotary evaporation
  3. dissolutionThe residue is dissolved in water
  4. temperatureunder cooling with ice
  5. extractionThe aqueous phase is extracted twice with EtOAc
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure

출처 및 근거

ORD 기록
ord-6fa0ac3b710f449dbac8da8885b9da4e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742132B2

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