Benzyl Bromide → HCID 15895031, compound

HRID 1954279Notes

Reaction equation

HRID 1954279 reaction equation
[CH3:1][C:2]1[O: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[O: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 343372,3-Dimethylfuran

Product 1

HCID 15895031HCID 15895031, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -78° C., to a stirred solution of commercial 2,3-dimethylfuran (50 g, 0.520 mol) in THF (2.6 L) was added dropwise 1.6M n-BuLi/hexanes (325 mL, 0.520 mol). After the addition was complete, the dry ice/acetone bath was removed and the reaction was stirred for 1 h. At -78° C., to the reaction was added dropwise commercial benzyl bromide (62 mL, 0.520 mol). After the addition was complete the reaction was stirred at -78° C. for 6 h, the dry ice/acetone bath was removed and the reaction was stirred for 7 days. The reaction was concentrated in vacuo and purified on silica gel eluting with hexane to give 75.70 g (78%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ 1.83 (s, 3 H), 2.08 (s, 3 H), 3.83 (s, 2 H), 5.83 (s, 1 H), 7.16-7.30 (m, 5 H). mass spectrum (EI), m/z 186 (M+).

Workup

  1. additionAfter the addition
  2. customthe dry ice/acetone bath was removed
  3. additionAfter the addition
  4. stirringwas stirred at -78° C. for 6 h
  5. customthe dry ice/acetone bath was removed
  6. stirringthe reaction was stirred for 7 days
  7. concentrationThe reaction was concentrated in vacuo
  8. custompurified on silica gel eluting with hexane

Sources & evidence

ORD record
ord-bbbb7b4059ff4ced81e2166906764541
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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