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

HRID 1919511Notes

Reaction equation

HRID 1919511 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH:11]([OH:16])[CH2:12][CH2:13][CH:14]=[CH2:15].[Br:17]N1C(=O)CCC1=O>C(Cl)Cl>[Br:17][CH2:15][CH:14]1[CH2:13][CH2:12][CH:11]([CH2:10][C:4]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[O:16]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674994761-(2'-Methoxy-5'-fluorophenyl)hex-5-en-2-ol

Product 1

HCID 674990602-(Bromomethyl)-5-(2'-methoxy-5'-fluorobenzyl)tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2′-methoxy-5′-fluorophenyl)hex-5-en-2-ol (1.35 g, 6.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added N-bromosuccinimide (NBS, 1.30 g, 7.2 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 (5% EtOAc in Hexane, Rf=0.12) to give in the trans isomer (663 mg, 36%) as an oil.

Workup

  1. customSolvent was then removed in vacuo
  2. customthe residue was purified by flash column chromatography (5% EtOAc in Hexane, Rf=0.12)
  3. customto give in the trans isomer (663 mg, 36%) as an oil

Sources & evidence

ORD record
ord-9b571283749b408aa76744aecb83cfbb
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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