5-Bromosalicylic acid → HCID 67107474, compound

HRID 1623647Notes

Reaction equation

HRID 1623647 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:9].[Br:10][C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:9])=[C:15]([CH:19]=1)[C:16]([O:18][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:9])=[O:17]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotoluene

Product 1

HCID 67107474HCID 67107474, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

1-(Bromomethyl)-2-chlorobenzene (833 mg, 4.05 mmol) was added dropwise to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (400 mg, 1.84 mmol) and potassium carbonate (509 mg, 3.69 mmol) in acetone (50 ml) over 1 min under nitrogen. The reaction mixture was stirred at 55° C. for 16 h. The organic phase was evaporated and the residue was washed with water (25 ml), extracted by ethyl acetate (3×30 ml) and evaporated in vacuo to yield the title compound as a light yellow solid. 520 mg.

Workup

  1. customThe organic phase was evaporated
  2. washthe residue was washed with water (25 ml)
  3. extractionextracted by ethyl acetate (3×30 ml)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c777de4ec7014d35a719636256113ee0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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