Benzoyl Peroxide → 2-(Bromomethyl)anthracene

HRID 1729463Notes

Reaction equation

HRID 1729463 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 119362-MethylanthraceneHCID 67184N-bromobutanimide

Product 1

HCID 190129612-(Bromomethyl)anthraceneYield 109.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methylanthracene (5.00 g, 26.25 mmol, 1 eq), N-bromosuccinimide (4.70 g, 26.25 mmol, 1 eq), benzoyl peroxide (1.0 g) and carbon tetrachloride (250 mL) were mixed and refluxed for 6 hours. The mixture was cooled to room temperature, and the succinimide precipitate filtered. The filtrate was evaporated to dryness and the residue taken up in ethyl acetate (250 mL) and washed with 1 N NaOH (3×200 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield 7.77 g of a light brown solid which was used without purification in the next step. NMR (DMSO-d6): δ 4.90 (s, 2H, CH2Br). ##STR55##

Workup

  1. temperaturerefluxed for 6 hours
  2. filtrationthe succinimide precipitate filtered
  3. customThe filtrate was evaporated to dryness
  4. washwashed with 1 N NaOH (3×200 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-28301d9a26ca4e53a6cc789a50c1282d
Source dataset
uspto-grants-1994_07
Patent number
US05332820

Reaction notes

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