N-bromobutanimide → 2-(Benzyloxy)-4-bromophenol

HRID 2247435Notes

Reaction equation

HRID 2247435 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:16])[CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide3×HCID 804592-Benzyloxyphenol

Product 1

HCID 218775142-(Benzyloxy)-4-bromophenolYield 89.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

12 g of 2-Benzyloxyphenol was dissolved in 300 ml of acetonitrile, 10.7 g of N-bromosuccinimide was added thereto, and the mixture was stirred at room temperature for 2 hours. Additional N-bromosuccinimide (1 g) was added thereto and the mixture was stirred for 1 hour, and further additional N-bromosuccinimide (1 g) was added thereto and the mixture was stirred for 2 hours. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 14.927 g of the title compound in the 10:1 hexane-ethyl acetate fraction.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6f3fa34a4b64417d82b21315866600d1
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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