1,2-Dibromoethane → 4-(2-Bromoethoxy)-3-fluorobenzonitrile

HRID 626227Notes

Reaction equation

HRID 626227 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[Br:17][CH2:18][CH2:19]Br>CN(C=O)C>[Br:17][CH2:18][CH2:19][O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 159788884-(2-Bromoethoxy)-3-fluorobenzonitrileYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 3-fluoro-4-hydroxybenzonitrile (1.2 g, 8.76 mmol), anhydrous K2CO3 (2.43 g, 17.6 mmol) and 1,2-dibromoethane (4.5 mL, 52.0 mmol) in DMF (6 mL) was stirred at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was filtered and extracted with ethyl acetate. The extract was washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1) to give 1.52 g (71%) of the subtitle compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=9.2 Hz, 1H), 7.40 (d, J=12.0 Hz, 1H), 7.03 (dd, J=8.0 Hz, 8.4 Hz, 1H), 4.42 (t, J=6.2 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-1f3657d34aa04471b676e18716cfc486
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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