Potassium Carbonate → 2-(3-(4-(Trifluoromethoxy)phenoxy) propyl) isoindoline-1,3-dione

HRID 522925Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[F:32][C:33]([F:43])([F:42])[O:34][C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1>CN(C=O)C>[F:32][C:33]([F:42])([F:43])[O:34][C:35]1[CH:40]=[CH:39][C:38]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:16](=[O:25])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]2=[O:24])=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-(1,3-dioxoisoindolin-2-yl)propyl 4-methylbenzenesulfonate (3 g, 8.35 mmol) in DMF (25 mL, 3 mL/mmol) was added potassium carbonate (1.8 g, 12.5 mmol) and 4-trifluoromethoxyphenol (1.5 g, 8.35 mmol) and the reaction was heated at 120° C. for 2 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×60 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 2-(3-(4-(trifluoromethoxy)phenoxy) propyl) isoindoline-1,3-dione (1 g, 33%) as a solid. Observed mass (M+1): 366.0.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×60 mL)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-7b49129670c74feeb1b9ca5c685a2a7e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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