Benzyl Bromide → Benzyl 2-bromoprop-2-enoate

HRID 1842929Notes

Reaction equation

HRID 1842929 reaction equation
[Br:1][C:2](=[CH2:6])[C:3]([OH:5])=[O:4].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][C:2](=[CH2:6])[C:3]([O:5][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 826332-Bromoacrylic acid2×

Product 1

HCID 13443472Benzyl 2-bromoprop-2-enoateYield 54.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-bromoacrylic acid (25.0 g, 166.66 mmol), benzyl bromide (21.8.0 mL, 183.32 mmol) and K2CO3 (46 g, 333.32 mmol) in acetonitrile (250 mL) was stirred at 80° C. for 3 h until complete consumption of 2-bromoacrylic acid, as evidenced by TLC analysis. The reaction mixture was filtered and concentrated. The obtained crude compound was purified by CC using 5% EtOAc in PE as eluent to afford benzyl 2-bromoacrylate (22 g, 53%) as a yellow liquid (TLC solvent system: 5% EtOAc in PE; Rf: 0.7).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe obtained crude compound
  4. customwas purified by CC

Sources & evidence

ORD record
ord-844f20ada75841b98184291a03b12b2c
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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