4-Iodobenzoic acid → Tert-butyl 4-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

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 light brown oil.

Provenance & Evidence