Benzyl Bromide → Methyl 4-(benzyloxy)-3,5-dichlorobenzoate

HRID 901142

反応式

HRID 901142 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([OH:11])=[C:6]([Cl:12])[CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([Cl:10])[CH:9]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 76856Methyl 3,5-dichloro-4-hydroxybenzoate

生成物 1

HCID 16749549Methyl 4-(benzyloxy)-3,5-dichlorobenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3,5-dichloro-4-hydroxy benzoic acid methyl ester (5.525 g, 25 mmol), benzyl bromide (5.13 g, 30 mmol) and potassium carbonate (6.91 g, 50 mmol) in N,N-dimethylformamide (100 mL) was stirred overnight at room temperature. The reaction mixture was poured into crushed ice (ca. 300 g) and the product was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. The solid residue was recrystallised from ethyl acetate and hexane. Yield: 7.47 g (96%) fine white needles. 1H-NMR (400 MHz, CDCl3) δ=3.93 (s, 3H, —OCH3), 5.12 (s, 2H, —CH2Ph), 7.35-7.44 (m, 3H), 7.54-7.58 (m, 2H), 8.01 (s, 2H). 13C-NMR (100 MHz, CDCl3) δ=52.66, 75.12, 127.18, 128.41, 128.48, 129.79, 130.13, 135.57, 154.57, 164.39.

後処理

  1. additionThe reaction mixture was poured
  2. extractionthe product was extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue was recrystallised from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-d12097e3ded04de19acd06caaa7c6ed2
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

関連ノート

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