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

HRID 882935Notes

Reaction equation

HRID 882935 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d129e1243ed9433980bb5e835b7f8e26
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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