Imidazole → 4-(2-Bromoethyl)-2-fluoro-1-methoxybenzene

HRID 1810015Notes

Reaction equation

HRID 1810015 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Br:25]Br.O[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1>C(Cl)Cl>[Br:25][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 27589993-Fluoro-4-methoxyphenethyl alcohol

Product 1

HCID 534041114-(2-Bromoethyl)-2-fluoro-1-methoxybenzeneYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of resin bound triphenyl phosphine (polystyrene 2% cross linking, loading=3 mmol/g, 3 g, 9 mmol) and imidazole (0.48 g, 7.1 mmol) in DCM (30 mL) cooled on an ice bath was drop wise added Br2 (1.13 g, 7.1 mmol), whereupon a solution of 4-(2-hydroxy-ethyl)-2-fluoro-1-methoxy-benzene (1.0 g, 5.88 mmol) in DCM (5 mL) was added. The cooling bath was removed and the reaction mixture was stirred for 16 hs before the resin was filtered off. The resin was washed with DCM and the filtrate was concentrated in vacuo. The residue was purified using column chromatography (SiO2, heptane-EtAOc 95:5) to give 0.82 g of 4-(2-bromo-ethyl)-2-fluoro-1-methoxy-benzene

Workup

  1. additionA mixture of resin
  2. temperaturecooled on an ice bath
  3. customThe cooling bath was removed
  4. filtrationwas filtered off
  5. washThe resin was washed with DCM
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-c0551eb6173e456eae4efd5ae274f767
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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