Acetic Acid → HCID 11036219, compound

HRID 1840002Notes

Reaction equation

HRID 1840002 reaction equation
[F:1][C:2]([F:15])([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O)[CH:3]([F:5])[F:4].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>O.ClCCCl>[Br:16][C:17]1[CH:18]=[C:19]([NH:20][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[C:7]([O:6][C:2]([F:15])([F:1])[CH:3]([F:5])[F:4])[CH:8]=2)[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 115623-BromoanilineHCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11036219HCID 11036219, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a 1,2-dichloroethane (30 mL) solution of 3-(1,1,2,2-tetrafluoroethoxy)-benzaldehyde (2.00 g, 9.0 mmol) was added 3-bromoaniline (0.98 mL, 9.0 mmol), NaB(OAc)3H (2.48 g, 11.7 mmol) and acetic acid (0.57 mL, 10 mmol). The cloudy mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 and brine, dried (MgSO4) and evaporated to yield 3.27 g (96%) of the desired N-(3-bromophenyl)-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amine product as a brown oil which was used without further purification. MS m/z=377 [M+].

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-7599c5cdfce643fc9fc76c41d400922d
Source dataset
uspto-grants-2004_01
Patent number
US06677375B2

Reaction notes

Loading…