Tetrahydrofuran → 2-[(5-Bromopentyl)oxy]-5-chlorobenzenepropanoic acid methyl ester

HRID 327941Notes

Reaction equation

HRID 327941 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]=[CH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Br:19].O1CCCC1.[H][H]>[Rh].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Br:19]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 538280543-[2-[(5-Bromopentyl)oxy]-5-chlorophenyl]-2-propenoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 543914602-[(5-Bromopentyl)oxy]-5-chlorobenzenepropanoic acid methyl esterYield 100.8%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2.02 g (5.59 mmol) of 3-[2-[(5-bromopentyl)oxy]-5-chlorophenyl]-2-propenoic acid methyl ester (mixture of E/Z isomers), 90 mL of tetrahydrofuran, 190 mL of toluene, and 1.26 g of 5% rhodium on alumina was stirred at room temperature, in an atmosphere of hydrogen, until reduction was complete. The catalyst was removed by suction filtration and the filtrate was concentrated in vacuo giving 2.05 g (ca. 100%) of 2-[(5-bromopentyl)oxy]-5-chlorobenzenepropanoic acid methyl ester as a pale-yellow oil which was used without further purification.

Workup

  1. customThe catalyst was removed by suction filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7239bf6c1db74d52b599f4d574a48ecf
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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