Bromine → HCID 86718768, compound

HRID 929588Notes

Reaction equation

HRID 929588 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-59ec1cdbd4de49d7ae4f618736792181
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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