Bromine → Methyl 4-(bromomethyl)-3-methoxybenzoate

HRID 1198187Notes

Reaction equation

HRID 1198187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].[Br:14]Br>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][Br:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Product 1

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 3-methoxy-4-methylbenzoate (10 grams) and 2,2-azobis(2-methyl-propionitrile) (25 milligrams) in carbon tetrachloride (200 mL) was heated to gentle reflux. Bromine (9 grams) was added in portions and resulting solution was heated at reflux for 1 hour then stirred at room temperature overnight. The carbon tetrachloride was evaporated and the residue dissolved in ether. The ether solution was washed with water. The ether layer was dried over sodium sulfate then evaporated to give 13.9 grams of crude product. NMR (CDCl3) δ:3.92 (s, 3H), 4.45 (s, 2H), 7.65-7.00 (m, 3H).

Workup

  1. customresulting solution
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. customThe carbon tetrachloride was evaporated
  5. dissolutionthe residue dissolved in ether
  6. washThe ether solution was washed with water
  7. dry with materialThe ether layer was dried over sodium sulfate
  8. customthen evaporated

Sources & evidence

ORD record
ord-dc317499ecd9492fb099c2a4f68c681e
Source dataset
uspto-grants-1994_01
Patent number
US05280039

Reaction notes

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