Boron tribromide → HCID 18614284, compound

HRID 2268123Notes

Reaction equation

HRID 2268123 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([CH3:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13]C)=[C:9]([CH:12]=1)[CH:10]=[O:11].B(Br)(Br)Br.C(OCC)(=O)C.O>ClCCl>[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([CH3:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 18614287HCID 18614287, compoundHCID 22728543Water ethylacetate

Product 1

HCID 18614284HCID 18614284, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.), stirred solution of 5-(2-chloro-6-methyl-4-nitro-phenoxy)-2-methoxy-benzaldehyde (10 g) in dichloromethane (300 mL) was added boron tribromide (23.3 g) dropwise. The reaction was allowed to warm to ambient temperature, stirred for 1.5 h, ice was added to quench the reaction and work up was done with ethyl acetate/water. The organic layer was dried over sodium sulfate, concentrated in vacuo and the resulting oil filtered through a plug of silica gel (eluting with chloroform) to afford 5-(2-chloro-6-methyl-4-nitro-phenoxy)-2-hydroxy-benzaldehyde (8.65 g) as an off-white solid.

Workup

  1. temperatureto warm to ambient temperature
  2. additionice was added
  3. customto quench
  4. customthe reaction and work
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. filtrationthe resulting oil filtered through a plug of silica gel (eluting with chloroform)

Sources & evidence

ORD record
ord-cb3a77097fe7427f9a3902ae6f4e5bbe
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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