Water → (4-benzyloxy-3-fluoro-phenyl)-acetic Acid Methyl Ester

HRID 1174788노트

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HRID 1174788 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([F:12])[CH:6]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([F:12])[CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

생성물 1

HCID 67205182(4-benzyloxy-3-fluoro-phenyl)-acetic Acid Methyl Ester수율 87.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of (3-fluoro-4-hydroxy-phenyl)-acetic acid methyl ester (15 g, 54.3 mmol) and benzyl bromide (9.28 g, 54.3 mmol) in DMF (50 mL), was K2CO3 (7.24 g, 54.3 mmol) added at an ambient temperature. The reaction mixture was heated to 60° C. and maintained for 2 hours. The reaction was cooled to room temperature and poured into H2O (150 mL). The organic compound was extracted with ether (150 mL) and washed with sat NaHCO3 (100 mL). The ether layer was dried over MgSO4, and concentrated under vacuum to afford the desired compound (12.9 g, 87.9%) as a white crystal. The crude compound was used for the next step without further purification. 1H NMR (400 Mz, DMSO-d6) δ 7.41-7.49 (m, 5H), 7.15-7.23 (m, 2H), 7.02-7.04 (m, 1H), 5.19 (s, 2H), 3.65 (s, 2H), 3.63 (s, 3H). LCMS 273.4 [MH+].

후처리

  1. additionadded at an ambient temperature
  2. temperaturemaintained for 2 hours
  3. temperatureThe reaction was cooled to room temperature
  4. extractionThe organic compound was extracted with ether (150 mL)
  5. washwashed
  6. dry with materialThe ether layer was dried over MgSO4
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-3800fc2aba484e5ba5695b8147834816
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838525B2

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