N-bromobutanimide → 1-(Benzyloxy)-4-bromo-2-ethyl-5-methoxybenzene

HRID 392869Notes

Reaction equation

HRID 392869 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=1[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([Br:26])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 226620992-(Benzyloxy)-1-ethyl-4-methoxybenzene

Product 1

HCID 226621061-(Benzyloxy)-4-bromo-2-ethyl-5-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a nitrogen atmosphere, 12.60 g (52.00 mmol) of 3-benzyloxy-4-ethyl-1-methoxybenzene (3) and 9.72 g (54.60 mmol) of NBS were combined in 350 mL of carbon tetrachloride, followed by the addition of 50 g of silica gel 60 (EM Science). The reaction was allowed to stir for 16 hours in the absence of light. The reaction mixture was filtered and the silica gel was washed with dichloromethane. The filtrate was washed with ethyl acetate (1×300 mL). The combined organic extracts were washed with 1M NaOH (2×300 mL), dilute NaHSO3 (1×200 mL) and brine (1×200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to yield 16.82 g (100%) of crude, 5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene (4) as a colorless oil.

Workup

  1. additionfollowed by the addition of 50 g of silica gel 60 (EM Science)
  2. filtrationThe reaction mixture was filtered
  3. washthe silica gel was washed with dichloromethane
  4. washThe filtrate was washed with ethyl acetate (1×300 mL)
  5. washThe combined organic extracts were washed with 1M NaOH (2×300 mL), dilute NaHSO3 (1×200 mL) and brine (1×200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ddf3c3ffce548a6b1852f758194725e
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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