Ethyl 4-amino-3-iodobenzoate → (4-Amino-3-iodophenyl)methanol

Temperature

0 °C

To a solution of ethyl 4-amino-3-iodobenzoate (8.0 g) in CH2Cl2 (56 mL) cooled to 0° C. is added diisobutylaluminum hydride in CH2Cl2 (110 mL of a 1M solution). The reaction is stirred at 0° C. for 2 h then quenched by the addition of MeOH (50 mL). To this is added 1N HCl (100 mL). The mixture is concentrated to remove the organics. The aqueous solution is extracted with CH2Cl2 (3×). The combined organic layers are dried over Na2SO4, filtered and condensed. The resulting residue is adsorbed onto silica and chromatographed (Biotage flash 40M, eluent CH2Cl2 (2L), 1% MeOH/CH2Cl2 (2L), 2% MeOH/CH2Cl2). Fractions homogeneous by TLC are combined and condensed to afford (4-amino-3-iodophenyl)methanol.

1. customthen quenched by the addition of MeOH (50 mL)
2. additionTo this is added 1N HCl (100 mL)
3. concentrationThe mixture is concentrated
4. customto remove the organics
5. extractionThe aqueous solution is extracted with CH2Cl2 (3×)
6. dry with materialThe combined organic layers are dried over Na2SO4
7. filtrationfiltered
8. customcondensed
9. customchromatographed (Biotage flash 40M, eluent CH2Cl2 (2L), 1% MeOH/CH2Cl2 (2L), 2% MeOH/CH2Cl2)
10. customcondensed

ORD record

ord-57402e57040a44be9a47e449cd982f7e

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06727248B2