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

HRID 1067337Notes

Reaction equation

HRID 1067337 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][C:4]2[O:3][C:2]([CH3:1])=[C:6]([CH3:7])[CH:5]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 343372,3-DimethylfuranHCID 685274-Bromobenzyl bromide

Product 1

HCID 234456202-(4-Bromo-benzyl)-4,5-dimethyl-furanYield 41.5%

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 4-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 5.72 g (41%) of the title compound. 1H NMR (DMSO-d6) δ1.84 (s, 3H), 2.09 (s, 3H), 3.83 (s, 2H), 5.87 (s, 1H), 7.17 (d, 2H), 7.49 (d, 2H).

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-db8cb295159347eeb7cf371040b0603d
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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