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

HRID 882935노트

반응식

HRID 882935 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d129e1243ed9433980bb5e835b7f8e26
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236808B2

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