2-Iodobenzoic acid → HCID 12413309, compound

HRID 400228Notes

Reaction equation

HRID 400228 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5]

Participants

5

Reactant 3

HCID 69412-Iodobenzoic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 12413309HCID 12413309, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 2-iodobenzoic acid (8.70 g, 35.1 mmol) and potassium carbonate (20.2 g, 176 mmol) in 100 mL of acetone was added benzyl bromide (5.00 g, 29.2 mmol). The mixture was stirred at room temperature for 23 hours and the solid was filtered off. The solid was rinsed with acetone (2×30 mL). The filtrate was concentrated in vacuo. The residue was dissolved in 200 mL of ether and washed with saturated sodium bicarbonate solution (2×50 mL) and brine (1×50 mL). The ether layer was dried (magnesium sulfate), filtered and concentrated in vacuo to give 8.63 g (87%) of benzyl 2-iodobenzoate A.

Workup

  1. filtrationthe solid was filtered off
  2. washThe solid was rinsed with acetone (2×30 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in 200 mL of ether
  5. washwashed with saturated sodium bicarbonate solution (2×50 mL) and brine (1×50 mL)
  6. dry with materialThe ether layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32ca527911d24999b675891293b5491c
Source dataset
uspto-grants-1998_10
Patent number
US05827868

Reaction notes

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