N-bromobutanimide → 2-(Bromomethyl)-5-(2'-methoxy-5'-fluorophenyl)tetrahydrofuran

HRID 1919509Notes

Reaction equation

HRID 1919509 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH:10]([OH:15])[CH2:11][CH2:12][CH:13]=[CH2:14].[Br:16]N1C(=O)CCC1=O>C(Cl)Cl>[Br:16][CH2:14][CH:13]1[CH2:12][CH2:11][CH:10]([C:4]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[O:15]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674998421-(2'-Methoxy-5'-fluorophenyl)pent-4-en-1-ol

Product 1

HCID 674991042-(Bromomethyl)-5-(2'-methoxy-5'-fluorophenyl)tetrahydrofuranYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2′-methoxy-5′-fluorophenyl)pent-4-en-1-ol (3.24 g, 18.0 mmol) in dry CH2Cl2 (50 mL) at 0° C. was added portionwise N-bromosuccinimide (NBS, 3.56 g, 20.0 mmol) portionwise and the reaction was warmed to room temperature for 12 h. Solvent was then removed in vacuo and the residue was purified by flash column chromatography (10% EtOAc in Hexane, Rf=0.28) to give the product (2.28 g, 44%) as an oil.

Workup

  1. customSolvent was then removed in vacuo
  2. customthe residue was purified by flash column chromatography (10% EtOAc in Hexane, Rf=0.28)

Sources & evidence

ORD record
ord-5cf6613acdeb4b2ab32af2cda0136a6e
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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