Imidazole → 2-(4-Bromobutyloxy)acetic acid methyl ester

HRID 1582222Notes

Reaction equation

HRID 1582222 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.N1C=CN=C1.[CH3:27][O:28][C:29](=[O:37])[CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35]O>C(Cl)Cl>[CH3:27][O:28][C:29](=[O:37])[CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][Br:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 86208818HCID 86208818, compound

Product 1

HCID 858402522-(4-Bromobutyloxy)acetic acid methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (5.59 g, 21.3 mmol), bromine (1.1 mL, 21.5 mmol) and imidazole (1.41 g, 20.7 mmol) were sequentially added to a solution of (4-hydroxy-butoxy)-acetic acid methyl ester (2.88 g, 17.8 mmol) in CH2Cl2 (15 mL) at 0° C. under nitrogen. After 1 h, the mixture was filtered through basic alumina, rinsing with 5% EtOAc/Hexane (40 mL). The filtrate was concentrated and the residue was purified by flash column chromatography (0%→20% EtOAc/Hexane) to afford 2.02 g (51%) of (4-bromo-butoxy)-acetic acid methyl ester as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through basic alumina
  2. washrinsing with 5% EtOAc/Hexane (40 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash column chromatography (0%→20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-18a2ca0383ee46b3a37c181411e8255d
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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