Benzyl Bromide → Benzyl 4-bromo-2-fluorobenzoate

HRID 432106Notes

Reaction equation

HRID 432106 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([F:19])[CH:11]=1.N12CCCN=C1CCCCC2>C(#N)C>[Br:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:15])=[C:12]([F:19])[CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 22351348Benzyl 4-bromo-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (0.86 g, 5.0 mmol, 1.1 eq.) was added neat to a solution of 4-bromo-2-fluorobenzoic acid. (1.0 g, 4.6 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.36 mL, 9.2 mmol, 2.0 eq.) in anhydrous acetonitrile (20 mL). The reaction was stirred at room temperature for 18 hours before removing the solvent in vacuo. The residue was diluted with ether and washed with water, saturated aqueous sodium bicarbonate, saturated aqueous ammonium chloride, and brine. The organic layer was dried (MgSO4) and concentrated in vacuo to provide the title compound as a pale yellow oil that crystallized into long needles upon standing (1.4 g, 99%): 1H NMR (300 MHz, CDCl3) δ 7.82 (t, 1H), 7.42-7.31 (m, 7H), 5.35 (s, 2H); GC/MS m/z 308/310 (M+ and M+2).

Workup

  1. custombefore removing the solvent in vacuo
  2. additionThe residue was diluted with ether
  3. washwashed with water, saturated aqueous sodium bicarbonate, saturated aqueous ammonium chloride, and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9e221c6c94644b8a1766210df500aef
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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