Bromine → HCID 86718768, compound

HRID 1854204Notes

Reaction equation

HRID 1854204 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[C:10]=2[OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8].C([O-])(=O)C.[Na+].[Br:23]Br>C(O)(=O)C>[Br:23][C:13]1[CH:12]=[C:11]([CH:15]=[O:16])[C:10]([OH:17])=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 532205553',4'-Dichloro-2-hydroxy[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 86718768HCID 86718768, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3′,4′-dichloro-2-hydroxy-[1,1′-biphenyl]-3-carbaldehyde (400 mg, 1.5 mmol) and sodium acetate (185 mg, 1.5 mmol) in acetic acid (20 mL), bromine (100 uL, 1.5 mmol) was added slowly. The resulted solution was stirred overnight. The reaction mixture was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL), washed with 5% aqueous sodium thiosulfate, the organic layer dried (MgSO4), filtered and concentrated under reduced pressure to give 5-bromo-3′,4′-dichloro-2-hydroxy-[1,1′-biphenyl]-3-carbaldehyde.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  3. washwashed with 5% aqueous sodium thiosulfate
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7bde8c1dd12418bb1f9e53b0dc69034
Source dataset
uspto-grants-2015_02
Patent number
US08962657B2

Reaction notes

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