Pyridine → 3-(2-Bromoethyl)-7-methoxybenzofuran

HRID 392151Notes

Reaction equation

HRID 392151 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13]O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]Br.N1C=CC=CC=1>C(Cl)Cl>[Br:34][CH2:13][CH2:12][C:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=2[O:10][CH:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 24408BromineHCID 226629353-(2-Hydroxyethyl)-7-methoxybenzofuran

Product 1

HCID 226629373-(2-Bromoethyl)-7-methoxybenzofuranYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared by the same method as for intermediate 25, using 4.15 g (21.6 mmol) of 2-(7-methoxybenzofuran-3-yl)-ethanol, 6.8 g (25.9 mmol) of triphenylphosphine, 1.34 mL (25.9 mmol) of bromine, and 3.5 mL (43.2 mmol) of pyridine in 70 mL of CH2Cl2, to afford 2.87 g (52%) of the title compound after flash chromatography on SiO2 (25% CH2Cl2/hexanes to 100% CH2Cl2 gradient): MS (ESI) m/z 254 [M]+.

Sources & evidence

ORD record
ord-2f3a75522b294378b020cd0f92905c72
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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