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

HRID 2377935ノート

反応式

HRID 2377935 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-27a15caa6f834761b4959ed1ab215d3c
出典データセット
uspto-grants-2008_12
特許番号
US07470699B2

反応ノート

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