Benzyl Bromide → 2,3-Dimethyl-5-benzylthiophene

HRID 1067355Notes

Reaction equation

HRID 1067355 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:8]([C:4]1[S:3][C:2]([CH3:1])=[C:6]([CH3:7])[CH:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 342952,3-Dimethylthiophene

Product 1

HCID 102419632,3-Dimethyl-5-benzylthiopheneYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 1 using 2,3-dimethylthiophene (5.00 g, 44.6 mmol), 2.5M BuLi/hexanes (17.9 mL, 44.6 mmol) and benzyl bromide (5.30 mL, 44.6 mmol) in THF (44.6 mL). Purification on Biotage KP-Sil eluting with 1% EtOAc/pet ether gave 6.96 g (77%) of the title compound as an oil. 1H NMR (DMSO-d6) δ2.01 (s, 3H), 2.21 (s, 3H), 3.98 (s, 2H), 6.58 (s, 1H), 7.18-7.37 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-ccbc07d4361548fbab202e7a752fde4c
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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