Trifluoroacetic acid → HCID 21501234, compound

HRID 1729753Notes

Reaction equation

HRID 1729753 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[P:11]([O:19]C1C=CC=CC=1)[O:12]C1C=CC=CC=1.[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[C:29]([F:35])[CH:28]=1.[CH3:36][NH:37][C:38]([NH:40][CH3:41])=[O:39].[OH-].[Na+].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.C(O)C.O>[CH3:36][N:37]([CH:31]([P:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:12])[OH:19])[C:30]1[CH:33]=[CH:34][C:27]([Br:26])=[CH:28][C:29]=1[F:35])[C:38]([NH:40][CH3:41])=[O:39]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7293N,N'-DimethylureaHCID 14798Sodium HydroxideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 21501257HCID 21501257, compound

Product 1

HCID 21501234HCID 21501234, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

When an equimolar mixture of diphenyl 2-napthylphosphonite, 4-bromo-2-fluorobenzaldehyde and 1,3-dimethylurea in toluene is warmed at reflux for 1 hour, followed by cooling in an ice bath, a white solid product forms. A portion of this solid is dissolved in ethanol and an equivalent amount of sodium hydroxide (10 molar solution) is added dropwise to the stirred solution. The reaction mixture is allowed to evaporate to dryness, and the residue is washed with ether, giving a crude sodium phosphinate salt. This salt is stirred in distilled water as slightly more than one equivalent of trifluoroacetic acid is added. The product is separated by filtration and then washed with water and recrystallized, giving [α-(1,3-dimethylureido)-4-bromo-2-fluorobenzyl]-2-naphthylphosphinic acid.

Workup

  1. temperatureis warmed
  2. temperatureat reflux for 1 hour
  3. temperatureby cooling in an ice bath
  4. customto evaporate to dryness
  5. washthe residue is washed with ether
  6. customgiving a crude sodium phosphinate salt
  7. additionis added
  8. customThe product is separated by filtration
  9. washwashed with water
  10. customrecrystallized

Sources & evidence

ORD record
ord-bcb0703c949d43babb24dffefaef5ae5
Source dataset
uspto-grants-1976_11
Patent number
US03989727

Reaction notes

Loading…