Potassium Carbonate → 1251459-19-4

HRID 2410506Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([CH:7]=1)[O:8][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-bromo-2,3-difluorophenol (Avocado, 2.5 g, 12.0 mmol) in DMF (50 mL) was added ethyl 4-bromobutyrate (2.57 g, 13.2 mmol) and K2CO3 (2.5 g, 18 mmol). The reaction mixture was heated at 80° C. for 3 hours. The reaction mixture was diluted with EtOAc and washed with water (3×) and brine, dried (MgSO4) and concentrated under vacuum affording the title compound as a colorless oil (3.53 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 7.36 (m, 1H), 7.28 (m, 1H), 4.16-4.03 (m, 4H), 2.45 (t, 2H), 2.03-1.94 (m, 2H), 1.18 (t, 3H). LC/MS (Method B): 323.1, 325.0 (M+H)+. HPLC (Method A) Rt 4.94 min (Purity: 99.8%).

Workup

washwashed with water (3×) and brine
dry with materialdried (MgSO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a51e70d2561a4338812df1219fdcead7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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