Sodium Hydroxide → HCID 19030235, compound

HRID 266655Notes

Reaction equation

HRID 266655 reaction equation
[OH-:1].[Na+].BrBr.[F:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16](C(=O)C)=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[F:12].S(=O)(O)[O-].[Na+].[O:27]1[CH2:32]COCC1>O>[F:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]=1[C:32]([OH:27])=[O:1]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 312751,4-DioxaneHCID 19030233HCID 19030233, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19030235HCID 19030235, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Next, to a mixture in which 530 g of ice and 125 g of water were added to 126 g of sodium hydroxide was gradually added dropwise 125 g of bromine. After completion of dropwise addition, a solution of the previously obtained 45 g of 3,4-difluoro-4'-acetylbiphenyl dissolved in 230 ml of dioxane was added dropwise to the mixture at a temperature of 20° C. or lower. After completion of the dropwise addition, the mixture was heated to 50° C. and reacted for 1 hour. After the reaction, 100 ml of a 40% aqueous sodium bisulfite solution was added to precipitate crystals. The crystals were collected by filtration, washed well with methanol and purified by recrystallization to obtain 36 g of 3,4-difluorobiphenyl carboxylic acid.

Workup

  1. additionAfter completion of dropwise addition
  2. additionwas added dropwise to the mixture at a temperature of 20° C.
  3. additionAfter completion of the dropwise addition
  4. customreacted for 1 hour
  5. additionwas added
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed well with methanol
  9. custompurified by recrystallization

Sources & evidence

ORD record
ord-73835a6a22b54db08ff221b78908e81d
Source dataset
uspto-grants-1997_07
Patent number
US05651919

Reaction notes

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