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

HRID 1919516Notes

Reaction equation

HRID 1919516 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH2:11][CH:12]([OH:17])[CH2:13][CH:14]=[CH:15][CH3:16].[Br:18]N1C(=O)CCC1=O>C(Cl)Cl>[Br:18][CH2:16][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10][C:4]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[O:17]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674997401-(5-Fluoro-2-methoxyphenyl)hept-5-en-3-ol

Product 1

HCID 674993232-(Bromomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2′-methoxy-5′-fluorophenyl)hept-5-en-3-ol (3.5 g, 14.7 mmol) in dry CH2Cl2 (90 mL) at 0° C. was added N-bromosuccinimide (NBS, 3.15 g, 17.0 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 (5% EtOAc in Hexane, Rf=0.12) to result in the trans isomer (2.05 g, 44%) as an oil; and the cis isomer (743 mg, 16%) as an oil; and mixture of both isomers (1.35 g, 29%).

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 result in the trans isomer (2.05 g, 44%) as an oil
  4. additionand mixture of both isomers (1.35 g, 29%)

Sources & evidence

ORD record
ord-bd272b23401f474f8bf54dfa10281f29
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

Loading…