Carbon tetrabromide → [4-(3-Bromo-propyl)-phenoxy]-acetic acid methyl ester

HRID 882935ノート

反応式

HRID 882935 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14]O)=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][Br:37])=[CH:8][CH:7]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

生成物 1

HCID 67028183[4-(3-Bromo-propyl)-phenoxy]-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [4-(3-Hydroxy-propyl)-phenoxy]-acetic acid methyl ester (2.45 g, 10.9 mmol) in DCM (60 mL) is added polymer-supported triphenylphosphine (7.26 g, 21.8 mmol) and carbon tetrabromide (3.47 g, 11.99 mmol) and the resulting reaction mixture is stirred at RT for 15 h. The reaction mixture is filtered to remove the polymer-supported reagent, and then concentrated in vacuo. The residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 1:5) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.14 (2H, d), 6.86 (2H, d), 4.69 (2H, s), 3.83 (3H, s), 3.40 (2H, t), 2.74 (2H, t), 2.15 (2H, m).

後処理

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture is filtered
  3. customto remove the polymer-supported reagent
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (SiO2, EtOAc:iso-hexane, 1:5)

出典と根拠

ORDレコード
ord-d129e1243ed9433980bb5e835b7f8e26
出典データセット
uspto-grants-2012_08
特許番号
US08236808B2

反応ノート

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