Isobutyraldehyde → HCID 59189444, compound

To a solution of 1,4-diiodo-2-nitrobenzene (2.24 g, 6.0 mmol) in anhydrous THF (20 mL) at minus 40° C. under a nitrogen atmosphere, phenylmagnesium bromide (2 M in THF, 3.2 mL, 6.4 mmol) was added dropwise at a rate that the temperature would not exceed minus 35° C. Upon completion of the addition the mixture was stirred for 5 minutes, followed by addition of isobutyraldehyde (0.726 mL, 8.0 mmol). The mixture was gradually warmed up to room temperature, quenched with saturated NH4Cl (8 mL), then poured into water (100 mL). The mixture was extracted three times with ethyl acetate (150 mL), and the combined organic phase was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to yield racemic (RS)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propanol (1.54 g, 80%) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.18 (d, 1 H, J=1.7 Hz, Ph-H), 7.93 (dd, 1 H, J=1.7 and 8.3 Hz, Ph-H), 7.50 (d, 1 H, J=8.3 Hz, Ph-H), 5.04 (m, 1 H, Ph-CH), 2.17 (d, 1 H, J=4.4 Hz, OH), 1.98 (m, 1 H, CH), 0.93 (d, 3 H, J=4.4 Hz, CH3), 0.92 (d, 3 H, J=4.4 Hz, CH3); 13C NMR (100 MHz, CDCl3): δ 148.62 (C), 141.81 (CH), 138.57 (C), 132.72 (CH), 130.49 (CH), 91.51 (C), 73.48 (CH), 34.22 (CH), 19.62 (CH3), 16.71 (CH3).

1. customexceed minus 35° C
2. additionUpon completion of the addition the mixture
3. customquenched with saturated NH4Cl (8 mL)
4. additionpoured into water (100 mL)
5. extractionThe mixture was extracted three times with ethyl acetate (150 mL)
6. washthe combined organic phase was washed with brine (100 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. custompurified by silica gel column chromatography

ORD record

ord-d17d2591ac0d4c68a5b89206098dcf9e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497360B2