Bromine → HCID 53657601, compound

HRID 1736496Notes

Reaction equation

HRID 1736496 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]Br>C(O)(=O)C>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Br:18])=[CH:12][C:11]=1[O:16][CH3:17])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 68272Guaiacol benzoate

Product 1

HCID 53657601HCID 53657601, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A stirred solution of 2-methoxyphenyl benzoate (29.1 g) in glacial acetic acid (150 mL) is treated with a solution of bromine (7.2 mL) in glacial acetic acid (25 mL) during a period of 20 minutes, and the solution is then stirred for a further period of 30 minutes at room temperature. The mixture is concentrated in vacuo, and the resulting residue is dissolved in methyl t-butyl ether (200 mL), washed with water (100 mL) and saturated aqueous sodium bicarbonate solution (3×100 mL), dried over magnesium sulphate and evaporated. The resulting residue is recrystallized from cyclohexane, to give 4-bromo-2-methoxyphenyl benzoate (22.7), m.p. 73°-75° C. [Elemental analysis: C,55.0; H,3.6; Br, 25.5%; calculated: C,54.6; H,3.9; Br, 25.9%].

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionthe resulting residue is dissolved in methyl t-butyl ether (200 mL)
  3. washwashed with water (100 mL) and saturated aqueous sodium bicarbonate solution (3×100 mL)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe resulting residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-14b16b007a83493cb2e0a63e06704b74
Source dataset
uspto-grants-1996_07
Patent number
US05541219

Reaction notes

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