Hydrochloric Acid → Benzyl 3-iodobenzoate

HRID 2097672Notes

Reaction equation

HRID 2097672 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120603-Iodobenzoic acid

Product 1

HCID 22254461Benzyl 3-iodobenzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-iodobenzoic acid (1.0 equiv) in dry DMF (0.5 M) under argon was added solid potassium carbonate (1.5 equiv) followed by benzyl bromide (1.1 equiv). The resulting mixture was stirred at rt for 4 h, acidified with 10% HCl, diluted with brine and ethyl acetate, and the layers were separated. The organic layer was washed with brine (5×), dried (MgSO4), filtered and concentrated in vacuo to afford a solid, benzyl 3-iodobenzoate (4), which was used without further purification.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine (5×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8645a71551c440592818f193c29261a
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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