5-Bromosalicylic acid → HCID 67106908, compound

HRID 1623635Notes

Reaction equation

HRID 1623635 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[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][C:6]([Cl:9])=[CH:5][CH:4]=2)=[C:15]([CH:19]=1)[C:16]([O:18][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1)=[O:17]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 67106908HCID 67106908, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

1-(Bromomethyl)-4-chlorobenzene (592 mg, 2.88 mmol) was added in a single charge to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (250 mg, 1.15 mmol) and potassium carbonate (478 mg, 3.46 mmol) in acetone (40 ml) under nitrogen at 20° C. The reaction mixture was stirred at 55° C. for 18 h. The organic phase was evaporated and the residue was washed with water (25 ml), extracted with ethyl acetate (30×3 ml) and evaporated in vacuo to yield the title compound as an off-white solid. 320 mg.

Workup

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

Sources & evidence

ORD record
ord-e1600262c5264bc9a32edb78a2f31b74
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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