Boron tribromide → 3,4-Dihydroxy-5-iodobenzaldehyde
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationwas then concentrated
- temperaturecooled to 0° C.
- customThe crystallized product was separated out
- washwashed with water
- customdried
- customcrystallized from an isopropanol-water mixture (1-2 by volume)
Sources & evidence
- ORD record
- ord-6fcdb714ffe2483e8574b31187fe9a39
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05763617
Reaction notes
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