Hydrochloric Acid → 4-Bromo-2-phenoxybenzoic acid

HRID 1803333Notes

Reaction equation

HRID 1803333 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8]C(C#N)=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1.[OH-:17].[Na+].Cl.[CH3:20][CH2:21][OH:22]>>[Br:1][C:2]1[CH:9]=[CH:8][C:20]([C:21]([OH:17])=[O:22])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 574366654-Bromo-2-phenoxybenzonitrile

Product 1

HCID 230539204-Bromo-2-phenoxybenzoic acid

Procedure

4-Bromo-2-phenoxy-benzonitrile (35.3 g, 129 mmol) was added to 130 mL EtOH, followed by the addition of 340 mL of 20% NaOH (aq). The reaction was heated to reflux for 20 h. The mixture was cooled to room temperature and poured into 6 N HCl to form a precipitate. The solid was collected by vacuum filtration and dissolved in 3:1 THF-ethyl ether and washed with brine. The organic phase was dried over magnesium sulfate, and concentrated. The solids were dried in a vacuum oven at 60° C. overnight to give 35.1 g (128 mmol) of the desired product. MS m/z (MH+) 292.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 h
  3. customto form a precipitate
  4. filtrationThe solid was collected by vacuum filtration
  5. dissolutiondissolved in 3:1 THF-ethyl ether
  6. washwashed with brine
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe solids were dried in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-7270b731c5fc46e899e4abc64dafcd0e
Source dataset
uspto-grants-2013_01
Patent number
US08350041B2

Reaction notes

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