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

HRID 1919536Notes

Reaction equation

HRID 1919536 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH2:8][CH2:9][CH:10]([OH:15])[CH2:11][CH2:12][CH:13]=[CH2:14])[CH:7]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)Cl>[Br:18][CH2:14][CH:13]1[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[O:15]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 252585767-(5'-Fluoro-2'-methoxyphenyl)hept-1-en-5-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8 (3.24 g, 18.0 mmol) in dry CH2Cl2 (50 mL) at 0° C. was added N-bromosuccinimide (3.56 g, 20.0 mmol) portion-wise and the reaction was warmed to room temperature and stirred for 12 h. Solvent was then removed in vacuo and the product was purified by flash column chromatography (EtOAc/hexane, 5:95, v:v, Rf=0.1) and resulted in a colorless oil as a 2:1 mixture of trans:cis diastereomers; 1H NMR (CDCl3, 500 MHz): δ 6.86-6.81 (m, 2 H), 6.72 (dd, J=4.6, 8.6 Hz, 1 H), 4.22 (m, 1 H), 4.03 (m, 1 H), 3.78 (s, 3H), 3.44 (dd, J=4.3, 9.7 Hz, 1 H), 3.34 (dd, J=6.4, 9.7 Hz, 1 H), 2.6 (t, J=7.3 Hz, 2 H), 2.13 (m, 1 H), 2.05 (m, 1 H), 1.75 (m, 1 H), 1.67-1.46 (m, 5 H).

Workup

  1. customSolvent was then removed in vacuo
  2. customthe product was purified by flash column chromatography (EtOAc/hexane, 5:95, v:v, Rf=0.1)
  3. customresulted in a colorless oil as a 2:1 mixture of trans

Sources & evidence

ORD record
ord-fe38bc9011b541eaaf4ada72be1db461
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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