Réaction #2487486

Équation de réaction

4-Iodobenzoic acid

→

4-Iodobenzoic Acid tert-butyl Ester

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe reaction was mixed for 16 h
2. 2
   Températurecooled from 70° C. to rt
3. 3
   TempératureThe solution was heated to 70° C. for and
4. 4
   workup.ADDITIONmixed for 5 h
5. 5
   ConcentrationThe sample was concentrated under vacuum, and AcOEt (400 ml)
6. 6
   workup.ADDITIONwas added
7. 7
   LavageThe solution was then washed with 1:1 sat. NaHCO3/water (150 ml), and sat. NaHCO3, water and sat. NaCl (75 ml each)
8. 8
   SéchageThe organic phase was dried (MgSO4)
9. 9
   Concentrationconcentrated under vacuum
10. 10
    Autreto yield a light brown oil

Mode opératoire

4-Iodobenzoic acid (10 g, 40.3 mmol) was dissolved in dry toluene (100 ml, dried over mol. sieves). The solution was heated to 70° C. under a flow of nitrogen. A solution of N,N′-dimethylformamide di-tert-butyl acetal (24.6 g, 121 mmol) in toluene (25 ml) was added over ca. 30 min. The reaction was mixed for 16 h. At some point the heating unit failed, So the reaction cooled from 70° C. to rt. The solution was heated to 70° C. for and mixed for 5 h. The sample was concentrated under vacuum, and AcOEt (400 ml) was added. The solution was then washed with 1:1 sat. NaHCO3/water (150 ml), and sat. NaHCO3, water and sat. NaCl (75 ml each). The organic phase was dried (MgSO4) and concentrated under vacuum to yield a light brown oil.

Source