Bromine → 5-Bromo-4-fluoro-2-hydroxybenzaldehyde
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.[Br:11]Br>CC(O)=O>[Br:11][C:9]1[C:2]([F:1])=[CH:3][C:4]([OH:10])=[C:5]([CH:8]=1)[CH:6]=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
Into a 20-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 4-fluoro-2-hydroxybenzaldehyde (545 g, 3.89 mol, 1.00 equiv) in AcOH (5 L), followed by the addition of Br2 (623 g, 3.90 mol, 1.00 equiv) dropwise with stirring at 0-5° C. The resulting solution was stirred overnight at room temperature, quenched by the addition of 3 L of saturated aqueous Na2SO3 and diluted with 6 L of ice/water. The solids were collected by filtration, washed with 2×1.5 L of water and dried to afford 145 g (crude) of 5-bromo-4-fluoro-2-hydroxybenzaldehyde as a yellow solid.
Workup
- customInto a 20-L 4-necked round-bottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- stirringThe resulting solution was stirred overnight at room temperature
- customquenched by the addition of 3 L of saturated aqueous Na2SO3
- additiondiluted with 6 L of ice/water
- filtrationThe solids were collected by filtration
- washwashed with 2×1.5 L of water
- customdried
Sources & evidence
- ORD record
- ord-01a57c2642fb4febb7760ff1e208e1a8
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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