Potassium Carbonate → 2-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)-6-fluorobenzonitrile

HRID 1685106Notes

Reaction equation

HRID 1685106 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[C:4]#[N:5].Br[CH2:12][CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:25]=[C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23](=[O:24])[N:15]1[CH2:14][CH2:13][CH2:12][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 27832162-Fluoro-6-hydroxybenzonitrile

Product 1

HCID 672652932-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)-6-fluorobenzonitrileYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-fluoro-6-hydroxybenzonitrile (411 mg, 3 mmol), 2-(3-bromopropyl)isoindoline-1,3-dione (885 mg, 3.3 mmol), and potassium carbonate (1.24 g, 9 mmol) were heated overnight at 70° C. in N,N-dimethylformamide (6 mL). The mixture was cooled, diluted with water, and the precipitate filtered and dried to give 922 mg of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.79-7.87 (m, 4H), 7.69 (td, J=8.6, 6.9 Hz, 1H), 7.01-7.07 (m, 2H), 4.22 (t, J=5.8 Hz, 2H), 3.79 (t, J=6.6 Hz, 2H), 2.11 (quin, J=6.1 Hz, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate filtered
  3. customdried

Sources & evidence

ORD record
ord-32e4642003fe4fa2bd595706a60b81fe
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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