Benzoyl Peroxide → 5-(Bromomethyl)-2-methoxy-1-(trifluoromethyl)naphthalene

HRID 615520Notes

Reaction equation

HRID 615520 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[C:4]=1[C:14]([F:17])([F:16])[F:15].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]2[C:14]([F:16])([F:15])[F:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 155687612-Methoxy-5-methyl-1-(trifluoromethyl)naphthalene

Product 1

HCID 132172995-(Bromomethyl)-2-methoxy-1-(trifluoromethyl)naphthaleneYield 106.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 2-methoxy-5-methyl-1-(trifluoromethyl)naphthalene (1.2 g, 5.0 mmol), N-bromosuccinimide (1.07 g, 6.0 mmol) and benzoyl peroxide (20-30 mg) in carbon tetrachloride (10 mL) was heated at reflux for 1.5 hr. The residual solid in the reaction mixture was removed by filration, and the collected solid on the filter was washed with methylene chloride. The combined filtrates were washed with water, dried (MgSO4) and evaporated to give 1.7 g of 5-(bromomethyl)-1-(trifluoromethyl)-2-methoxynaphthalene (IX, R=CH3 and R1 =CH2Br) which was used in the next step without purification. Crystallization of a sample from hexane furnished pure 5-(bromomethyl)-1-trifluoromethyl-2-methoxynaphthalene having mp 97°-99° C.; nmr (CDCl3) δ 3.95 (s, 3H), 4.85 (s, 2H), 7.7 (m, 5H); ir (CHCl3) 1265, 1125 cm-1 ; uvλmax (MeOH) 339 nm (ε 3,510), 326 (3,280), 300 (7,230), 288 (7,150), 229 (44,150); Anal Calcd for C13H10BrF3O: C, 48.93% H, 3.16%; Found: C, 48.88% H, 3.14%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hr
  3. customThe residual solid in the reaction mixture was removed by filration
  4. washthe collected solid on the filter was washed with methylene chloride
  5. washThe combined filtrates were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-12f997b20e8e4161b8e565954695e3fb
Source dataset
uspto-grants-1985_02
Patent number
US04499310

Reaction notes

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