N-Hydroxyphthalimide → N-(3-Trifluoromethylphenoxy)phthalimide

HRID 971172Notes

Reaction equation

HRID 971172 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[OH:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25]>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:14][N:15]1[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]2[C:19]1=[O:20]

Participants

3

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 11266782N-(3-Trifluoromethylphenoxy)phthalimideYield 88%

Procedure

3-Trifluoromethylphenylboronic acid (380 mg, 2.0 mmol) was subjected to the representative coupling procedure with N-hydroxyphthalimide (NHP) as outlined above (method 1). Flash chromatographic purification over silica (40% EtOAc in hexanes) afforded 10 as a white solid (270 mg, 88%). 1H-NMR (500 MHz, CDCl3) δ 7.34-7.38 (m, 1H), 7.40-7.45 (m, 2H), 7.47 (m, J=0.9, 8.1 Hz, 1H), 7.82-7.87 (m, 2H), 7.92-7.97 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 111.6, 117.8, 118.1, 121.4, 122.3, 124.2, 128.8, 130.5, 132.2, 135.1, 159.0, 162.8; LC-MS 309 m/z [MH]+, C15H9F3NO3 requires 309.

Workup

  1. customFlash chromatographic purification over silica (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-039d8dada9874edfa04deb05e6deb7c5
Source dataset
uspto-grants-2007_12
Patent number
US07312361B2

Reaction notes

Loading…