Boron tribromide → 3,4-Dihydroxy-5-iodobenzaldehyde

HRID 1081932

Reaction equation

HRID 1081932 reaction equation
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10]C)[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([OH:10])[C:3]=1[OH:12])[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 140282113,4-Dihydroxy-5-iodobenzaldehydeYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

37.2 g of 5-iodo vanillin (commercial) and 360 ml of dichloromethane were mixed together under nitrogen and the mixture was cooled to 0° C. 135 ml of a molar solution of boron tribromide in dichloromethane were added and the mixture stood for 16 hours at ambient temperature and was then concentrated, cooled to 0° C. and acidified. The crystallized product was separated out, washed with water, dried and crystallized from an isopropanol-water mixture (1-2 by volume) to obtain 23.4 g of the expected product.

Workup

  1. concentrationwas then concentrated
  2. temperaturecooled to 0° C.
  3. customThe crystallized product was separated out
  4. washwashed with water
  5. customdried
  6. customcrystallized from an isopropanol-water mixture (1-2 by volume)

Sources & evidence

ORD record
ord-64998333117e4317ad3210176b230909
Source dataset
uspto-grants-1996_12
Patent number
US05587372

Linked notes

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