1-Bromo-2-(bromomethyl)-4-fluorobenzene → HCID 79022360, compound

HRID 921213Notes

Reaction equation

HRID 921213 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4]Br.[CH2:11]([Mg]Br)[CH:12]=[CH2:13]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4][CH2:13][CH:12]=[CH2:11]

Participants

4

Reactant 2

HCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzeneHCID 178455850HCID 178455850, compound

Product 1

HCID 79022360HCID 79022360, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-fluorobenzyl bromide (1 g, 3.73 mmol) in THF (15 mL) was added allylmagnesium bromide (5.60 mL, 5.60 mmol) at 0° C. It was warmed to rt and then refluxed for 5 h. The reaction mixture was quenched with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil. It was then purified by 5% EtOac/hexane to isolate 1-bromo-2-(but-3-en-1-yl)-4-fluorobenzene (0.7 g, 3.06 mmol, 82% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.53-7.45 (m, 1H), 6.99-6.94 (m, 1H), 6.82 (td, J=8.3, 2.9 Hz, 1H), 5.89 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.14-4.98 (m, 2H), 2.89-2.76 (m, 2H), 2.45-2.33 (m, 2H).

Workup

  1. temperaturerefluxed for 5 h
  2. customThe reaction mixture was quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain an oil
  8. customIt was then purified by 5% EtOac/hexane

Sources & evidence

ORD record
ord-a156815f2a1e47e3a83e3a3a7e020814
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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