Water → HCID 11175955, compound

HRID 2262757Notes

Reaction equation

HRID 2262757 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24])=[O:15].B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:24])([F:25])[F:26])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86609606HCID 86609606, compound

Product 1

HCID 11175955HCID 11175955, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea (1 g) was dissolved in dry dichloromethane (20 ml) and cooled in an ice-bath. A 1M solution of BBr3 in dichloromethane (4 ml) was added drop-wise, and the solution stirred at room temperature for 30 minutes. Water was added, and after vigorous stirring, the mixture was extracted with dichloromethane. Drying (MgSO4), filtration, concentration in vacuo and flash chromatography provided a product which was slurried with petrol, filtered, washed with petrol and dried to afford 1-(2-Hydroxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea (340 mg). Mp.=158-159° C.

Workup

  1. temperaturecooled in an ice-bath
  2. extractionafter vigorous stirring, the mixture was extracted with dichloromethane
  3. customDrying
  4. filtration(MgSO4), filtration, concentration in vacuo and flash chromatography
  5. customprovided a product which
  6. filtrationfiltered
  7. washwashed with petrol
  8. customdried

Sources & evidence

ORD record
ord-553f567a981e44dd86bed7ebbb58d090
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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