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

HRID 1280892Notes

Reaction equation

HRID 1280892 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][CH:14]=[CH:13][C:10]=1[CH2:11]Br>C1COCC1>[Br:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][C:4]1[O:3][C:2]([CH3:1])=[C:6]([CH3:7])[CH:5]=1

Participants

4

Reactant 2

HCID 343372,3-DimethylfuranHCID 769652-Bromobenzyl bromide

Product 1

HCID 120939412-(2-Bromo-benzyl)4,5-dimethyl-furanYield 41.3%

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 (1.00 g, 10.4 mmol), commercial 2-bromobenzylbromide (2.60 g, 10.4 mmol) and 1.6M n-BuLi/hexanes (4.16 mL, 10.4 mmol) in THF. Purification on Biotage KP-Sil eluting with 100% pet. ether gave 1.14 g (41%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ 1.84 (s, 3H), 2.11 (s, 3H), 3.96 (s, 2H), 5.81 (s, 1H), 7.19 (dt, 1H), 7.26-7.37 (m, 2H), 7.60 (dd, 1H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage
  3. washKP-Sil eluting with 100% pet. ether

Sources & evidence

ORD record
ord-3977f04870a34d34ab205491d4ab31fc
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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