Benzyl Bromide → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 270929

反応式

HRID 270929 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

生成物 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 15 g (90.3 mmol) of methyl 4-hydroxyphenylacetate in 25 mL of dimethylformamide (DMF) was added 32.4 g (99.3 mmol) of cesium carbonate, followed by 13.4 mL (112.9 mmol) of benzyl bromide (BnBr), and the resulting heterogeneous mixture was stirred at rt for 72 h. The reaction mixture was filtered, the solids were washed with ethyl acetate, and the combined organic extracts were concentrated to give a residue which was chromatographed on silica gel (25% hexane in dichloromethane) to afford 19.1 g (83% yield) of desired (4-benzyloxy-phenyl)-acetic acid methyl ester as indicated by 1H NMR; LC-MS—calcd for C16H16O3 [M++H]+: 257.11, found: 257.2.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with ethyl acetate
  3. concentrationthe combined organic extracts were concentrated
  4. customto give a residue which
  5. customwas chromatographed on silica gel (25% hexane in dichloromethane)

出典と根拠

ORDレコード
ord-a54f2345cbbd4689a0409ce090346a3a
出典データセット
uspto-grants-2008_11
特許番号
US07449488B2

関連ノート

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