Sulfuric Acid → 1-Bromo-2-ethyl-4-[(phenylmethyl)oxy]benzene

HRID 1064908Notes

Reaction equation

HRID 1064908 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].OS([O-])=O.[Na+]>C1COCC1.C(OCC)(=O)C>[Br:17][C:8]1[CH:7]=[CH:6][C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[CH2:1][CH3:2]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 197444851-(Benzyloxy)-3-ethylbenzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 151434711-Bromo-2-ethyl-4-[(phenylmethyl)oxy]benzeneYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-ethyl-3-(phenylmethoxy)-benzene (15 g, 71 mmol) in THF (200 ml) were added N-bromosuccinimide (16.3 g, 92 mmol) and concentrated sulfuric acid (2.4 ml). The solution was stirred for 5 h at ambient temperature. Sodium bicarbonate (3.6 g) and 10% aqueous NaHSO3 solution (400 ml) were added under ice cooling. The resulting mixture was stirred for 10 min and then poured into ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were washed with ice water and brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, cyclohexane) to yield 17.1 g (58.7 mmol, 83%) of the title compound as colorless liquid.

Workup

  1. stirringThe resulting mixture was stirred for 10 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined extracts were washed with ice water and brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. customgave a yellow oil which
  8. customwas purified by column chromatography (silica gel, cyclohexane)

Sources & evidence

ORD record
ord-d448a34e780448448cc5a84ac8db2f88
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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