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

HRID 402918ノート

反応式

HRID 402918 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-6fa0ac3b710f449dbac8da8885b9da4e
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

反応ノート

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