Sodium Hydroxide → (2-Amino-4-methoxy-5-methylphenyl) (2,6-difluorophenyl)methanol

HRID 747609Notes

Reaction equation

HRID 747609 reaction equation
ClB(Cl)C1C=CC=CC=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[CH3:19])[NH2:15].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH:23]=[O:24].[OH-].[Na+]>ClCCl.C(OCC)C.O.C(N(CC)CC)C>[NH2:15][C:14]1[CH:13]=[C:12]([O:11][CH3:10])[C:18]([CH3:19])=[CH:17][C:16]=1[CH:23]([C:22]1[C:21]([F:20])=[CH:28][CH:27]=[CH:26][C:25]=1[F:29])[OH:24]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 278823-Methoxy-4-methylanilineHCID 1362842,6-DifluorobenzaldehydeHCID 136678Borane, dichlorophenyl-

Product 1

HCID 68567654(2-Amino-4-methoxy-5-methylphenyl) (2,6-difluorophenyl)methanolYield 47.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

To 6.05 g of dichlorophenylborane dissolved in 40 ml of dichloromethane, at −20° C., are successively added 5.226 g of 3-methoxy-4-methylaniline dissolved in 50 ml of dichloromethane, and 13.4 ml of triethylamine dissolved in 25 ml of dichloromethane. After 30 minutes at −20° C., 5.412 g of 2,6-difluorobenzaldehyde dissolved in 60 ml of dichloromethane are introduced. After 24 hours at room temperature, the mixture is hydrolysed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. To the oil obtained, dissolved in 80 ml of diethyl ether, are added 80 ml of 2M sodium hydroxide solution and the mixture is left stirring for 18 hours. The phases are separated by settling and the organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with n-pentane to give 5.069 g of the expected product.

Workup

  1. additionare introduced
  2. waitAfter 24 hours at room temperature
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customTo the oil obtained
  6. waitthe mixture is left
  7. customThe phases are separated
  8. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c8da1393febc473bac500a480f1264df
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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