Water → 5-Bromovanillin

HRID 2260378Notes

Reaction equation

HRID 2260378 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[Br:12]Br.O>C(O)(=O)C>[Br:12][C:10]1[C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=[C:3]([CH:11]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1183Vanillin2×HCID 24408Bromine

Product 1

HCID 180995-Bromovanillin

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In a 250 mL round bottom flask vanillin (Aldrich, 33.3 g, 0.22 moles) was dissolved in glacial acetic acid (100 mL) with stirring. A solution of bromine (Baker, 35.0 g, 0.43 mol, 11.2 mL) in glacial acetic acid (100 mL) was added to the solution of vanillin. After 5 min a precipitate formed but the reaction was allowed to stir for an additional 15 min. The solid was collected by filtration giving 18.2 g, 35%. The filtrate was then slowly added to water (300 mL) and allowed to stand overnight. The resulting solid was filtered and dried under vacuum giving additional product (18.4 g, 35%, total yield 36.6 g, 70%), mp 159°-163° C. (lit, 163°-164° C.), 1H NMR (CDCl3) δ3.99 (s, 3H), 6.61 (bs, 1H), 7.36 (d, J=1.3 Hz, 1H), 7.64 (d, J=1.3 Hz, 1H), 9.79 (s, 1H).

Workup

  1. customAfter 5 min a precipitate formed
  2. stirringto stir for an additional 15 min
  3. filtrationThe solid was collected by filtration
  4. customgiving 18.2 g, 35%
  5. filtrationThe resulting solid was filtered
  6. customdried under vacuum
  7. customgiving additional product (18.4 g, 35%, total yield 36.6 g, 70%), mp 159°-163° C. (lit, 163°-164° C.), 1H NMR (CDCl3) δ3.99 (s, 3H), 6.61 (bs, 1H), 7.36 (d, J=1.3 Hz, 1H), 7.64 (d, J=1.3 Hz, 1H), 9.79 (s, 1H)

Sources & evidence

ORD record
ord-a85ca7b75e9b4570b8ad85932c6056d2
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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