Hydroquinone → 4-Bromo-1-fluoro-2-isopropenyl-benzene

HRID 2196278Notes

Reaction equation

HRID 2196278 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:8](O)([CH3:10])[CH3:9])[CH:7]=1.C1C(O)=CC=C(O)C=1.OP(O)(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:7]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 1004Phosphoric AcidHCID 666653182-(5-Bromo-2-fluorophenyl)propan-2-ol

Product 1

HCID 585629224-Bromo-1-fluoro-2-isopropenyl-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(5-bromo-2-fluoro-phenyl)-propan-2-ol (119.7 g, 498 mmol) in CH2Cl2 (50 ml) was added hydrochinone (2.74 g, 24.9 mmol) and 250 ml 85% H3PO4. The resulting reaction mixture was stirred for 3.5 h at 50° C. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phases were washed with 2N aqueous NaOH and water, dried over MgSO4, filtered and concentrated. The crude product was dissolved in hexane and filtered through a plough of silica gel to obtain after concentration at 600 mbar the title compound as a colorless oil: TLC (hexane): Rf=0.52; UPLC RtH5=1.416 min; 1H NMR (360 MHz, CDCl3): δ 7.43 (dd, 1H), 7.37 (m, 1H), 6.94 (dd, 1H), 5.27 (d, 2H), 2.13 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. additionThe mixture was poured onto ice-water
  3. extractionextracted with CH2Cl2
  4. washThe organic phases were washed with 2N aqueous NaOH and water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe crude product was dissolved in hexane
  9. filtrationfiltered through a plough of silica gel
  10. customto obtain
  11. concentrationafter concentration at 600 mbar the title compound as a colorless oil
  12. customUPLC RtH5=1.416 min

Sources & evidence

ORD record
ord-fc700c1b21974a27a8b4fdeffc3d5631
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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