Dimethylformamide → HCID 22934559, compound

HRID 1354408Notes

Reaction equation

HRID 1354408 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)[CH:28]=[O:29]>O>[CH2:12]([O:11][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:10][C:6]=1[C:7]([O:29][CH2:28][C:2]1[CH:10]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 83885-Iodosalicylic acidHCID 11430Potassium Carbonate

Product 1

HCID 22934559HCID 22934559, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-iodosalicylic acid (6.60 g), benzyl bromide (6.54 ml), potassium carbonate (13.8 g) and N,N-dimethylformamide (100 ml) was stirred at room temperature for 2 hrs. and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed three times with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio), and crystallized from hexane-ethyl acetate to give benzyl 2-benzyloxy-5-iodobenzoate (7.75 g, yield 70%) as colorless plate crystals. melting point: 72–73° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed three times with water
  3. dry with materialonce with saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio)
  6. customcrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4dc71c84a5364eceb784ef7ff8f95454
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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