4-Iodobenzoic acid → Tert-butyl 4-iodobenzoate

Temperature

70 °C

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.

1. additionThe reaction was mixed for 16 h
2. temperaturecooled from 70° C. to rt
3. temperatureThe solution was heated to 70° C. for and
4. additionmixed for 5 h
5. concentrationThe sample was concentrated under vacuum, and AcOEt (400 ml)
6. additionwas added
7. washThe solution was then washed with 1:1 sat. NaHCO3/water (150 ml), and sat. NaHCO3, water and sat. NaCl (75 mL each)
8. dry with materialThe organic phase was dried (MgSO4)
9. concentrationconcentrated under vacuum
10. customto yield light brown oil

ORD record

ord-d13a88f412aa44bda292cbcd2d52244d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933021B2