1,2-Dibromoethane → HCID 89656467, compound

HRID 626112Notes

Reaction equation

HRID 626112 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[Br:13][CH2:14][CH2:15]Br.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:15][CH2:14][Br:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 89656467HCID 89656467, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 3-bromo-4-hydroxybenzoate (5.0 g, 1.0 eq) in 20 mL DMF were added BrCH2CH2Br (11 mL, 6.0 eq) and K2CO3 (6.0 g, 2.0 eq). The mixture was heated to 60° C. for 6 h and purified by column chromatography with petroleum ether:EtOAc=3:1 to give the desired product (6.0 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 7.96 (d, J=8.8 Hz, 1H), 6.90 (d, J=8.8 Hz, 1H), 4.40 (t, J=6.8 Hz, 2H), 3.90 (s, 3H), 3.71 (t, J=6.4 Hz, 2H)

Workup

  1. custompurified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-48a27eebbd4a4a57a97a0aaa45008a39
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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