5-Bromosalicylic acid → HCID 67107173, compound

HRID 1623705Notes

Reaction equation

HRID 1623705 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F: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[F: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[F:9])=[O:17]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 67107173HCID 67107173, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

Neat 1-(bromomethyl)-2-fluorobenzene (1533 mg, 8.11 mmol) was added over 1 min to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (800 mg, 3.69 mmol) and potassium carbonate (1274 mg, 9.22 mmol) in acetone (60 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was filtered. The filtrate was evaporated and the residue was dissolved in diethyl ether (30 ml) and evaporated again. The residue was dried in vacuo to yield the title compound as a white solid. 1.74 g.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in diethyl ether (30 ml)
  4. customevaporated again
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-5038285157c84ec6bd13c7e95a0083a4
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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