4-Chloro-2-fluoro-1-nitrobenzene → 5-Chloro-2-nitroaniline

Amino-(4-methoxyphenyl)-methylpolystyrene (loading 1.69 mmol/g, 7.00 g, 11.8 mmol) was soaked in DMSO in a peptide vessel for 30 min. The solvent was then drained. DIEA (11.3 mL, 65.1 mmol) in DMSO (88 mL) was added to the resin, followed by 4-chloro-2-fluoronitrobenzene (10.4 g, 59.2 mmol). The mixture was shaken at room temperature for 19 h, at which point it was drained. The resin was washed with DMSO (3×), EtOH (3×), DMF (3×), MeOH (3×) and DCM (3×). It was then dried under vacuum overnight. A small sample (approx. 10 mg) was treated with 23:2:75 (v/v/v) TFA/H2O/DCM (0.5 mL) for ca. 1 h. The solution containing the released material was concentrated and analyzed with LC/MS. UV (254 nm): 97% @ 5.65 min. MS: m/e 171 (M−1).

1. washThe resin was washed with DMSO (3×), EtOH (3×), DMF (3×), MeOH (3×) and DCM (3×)
2. customIt was then dried under vacuum overnight
3. additionA small sample (approx. 10 mg) was treated with 23:2:75 (v/v/v) TFA/H2O/DCM (0.5 mL) for ca. 1 h
4. additionThe solution containing the released material
5. concentrationwas concentrated
6. custom97% @ 5.65 min

ORD record

ord-a803f88ffc3f4bea85022cf638f3d0bc

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238813B2