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

HRID 1881077
Notes
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Reaction equation

HRID 1881077 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
2×

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-dd6f448f1c0545b5bd7c1086a920cd8f
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318778B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes