Bromine → 2-Bromo-1,4-dimethoxynaphthalene

HRID 280492Notes

Reaction equation

HRID 280492 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][CH:4]=1.[Br:15]Br>C(O)(=O)C>[Br:15][C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 823371,4-Dimethoxynaphthalene

Product 1

HCID 117804862-Bromo-1,4-dimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 50 grams (0.26 mol) of 1,4-dimethoxynaphthalene, prepared according to the procedure of L. Fieser, in the Journal of the American Chemical Society, Volume 70, page 3165 (1948), in 500 ml glacial acetic acid is added 13.7 ml (0.26 mol) of bromine at room temperature. The mixture is stirred for 1 hour, and the solvent is removed under reduced pressure and the residue dissolved in ether. The resulting solution is carefully washed twice with sodium bicarbonate, the organic layer separated, dried over sodium sulfate and the solvent removed. Distillation of the residue gave 63.4 grams (81% of theoretical yield) of liquid 2-bromo-1,4-dimethoxy-naphthalene (boiling 200°-210° at 0.1 mm Hg). The product has a nuclear magnetic resonance spectrum consistant with the expected structure and has peaks expressed in parts per million relative to tetramethylsilane at 8.0 (m,2H), 7.4(m,2H), 6.9(s,1H), 3.9(d,6H).

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved in ether
  3. washThe resulting solution is carefully washed twice with sodium bicarbonate
  4. customthe organic layer separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed
  7. distillationDistillation of the residue
  8. customgave

Sources & evidence

ORD record
ord-3200e8da074f4e89982dddb2bb1b2d67
Source dataset
uspto-grants-1986_05
Patent number
US04590063

Reaction notes

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