Water → Benzyl 3-iodobenzoate

HRID 1925581Notes

Reaction equation

HRID 1925581 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.O>CN(C=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

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120603-Iodobenzoic acid

Product 1

HCID 22254461Benzyl 3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodobenzoic acid (12.4 g) was dissolved in DMF (100 mL) and potassium carbonate (7.6 g) was added. Benzyl bromide (6.5 mL) was then added dropwise over approximately 10 minutes causing a slight exotherm to 24° C. The suspension was stirred at room temperature for 1.5 hours. The suspension was then poured into water (approximately 300 mL) and was extracted with diethyl ether. The combined organic phase was back washed with water and brine and dried over sodium sulfate. The solvent was stripped to yield a crude product as a colourless oil (17.0 g). The crude product was applied to a silica gel column and was eluted with cyclohexane-ethyl acetate (95:5) to give a colourless oil (13.08 g).

Workup

  1. customto 24° C
  2. extractionwas extracted with diethyl ether
  3. washThe combined organic phase was back washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customto yield a crude product as a colourless oil (17.0 g)
  6. washwas eluted with cyclohexane-ethyl acetate (95:5)

Sources & evidence

ORD record
ord-f87967c2a1c341a99d0d038afc3cdd24
Source dataset
uspto-grants-2012_05
Patent number
US08178573B2

Reaction notes

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