2,3-Dimethylfuran → 2-(3-Bromo-benzyl)4,5-dimethyl-furan

HRID 1871307Notes

Reaction equation

HRID 1871307 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br>C1COCC1>[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][C:4]1[O:3][C:2]([CH3:1])=[C:6]([CH3:7])[CH:5]=1

Participants

4

Reactant 2

HCID 343372,3-DimethylfuranHCID 699793-Bromobenzyl bromide

Product 1

HCID 234456292-(3-Bromo-benzyl)4,5-dimethyl-furanYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 1 using commercial 2,3-dimethylfuran (5.00 g, 52.0 mmol), commercial 3-bromobenzylbromide (13.0 g, 52.0 mmol) and 2.5M n-BuLi/hexanes (20.8 mL, 52.0 mmol) in THF. Purification on Biotage KP-Sil eluting with 1% EtOAc/pet. ether gave 12.63 g (85%) of the title compound. 1H NMR (DMSO-d6) δ 1.85 (s, 3 H), 2.10 (s, 3 H), 3.86 (s, 2 H), 5.90 (s, 1 H), 7.21-7.30 (m, 2 H), 7.34-7.47 (m, 2 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage
  3. washKP-Sil eluting with 1% EtOAc/pet. ether

Sources & evidence

ORD record
ord-24ad30fd666345259cf17fe85789d0e3
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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