Acetic Acid → HCID 18407223, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH:10](O)[C:11](F)(F)F)[CH:5]=[CH:6][CH:7]=1.[F:16][C:17]([F:28])([F:27])[O:18][C:19]1[CH:20]=C(C=[CH:25][CH:26]=1)C=O.[C:29]([OH:32])(=O)[CH3:30].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl.[OH-].[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:29]([OH:32])([CH3:30])[C:17]([F:28])([F:27])[F:16])[CH2:9][C:10]2[CH:11]=[CH:25][CH:26]=[C:19]([O:18][C:17]([F:16])([F:27])[F:28])[CH:20]=2)[CH:5]=[CH:6][CH:7]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
EX-633B) The 3-[(3-bromophenyl)amino]-1,1,1-trifluoro-2-propanol (1.14 g, 4 mmol) from EX-633A and 3-(trifluoromethoxy)benzaldehyde (0.78 g, 4.1 mmol) were dissolved in dichloroethane (18 mL). Acetic acid (0.253 mL, 4.2 mmol) and solid NaBH(OAc)3 (1.07 g, 5.05 mmol) were added. The mixture was stirred at room temperature for 3 h. then acidified with 1 N HCl solution. After neutralizing to pH 7.5 with 2.5 N sodium hydroxide, the mixture was extracted with methylene chloride. The organic layer was washed with brine and water, then dried over anhydrous MgSO4, and evaporated to give 1.12 g (62%) of the desired N-3-bromophenyl-[[[3-(trifluoromethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a brown oil, which was greater than 80% pure by reverse phase HPLC analysis. HRMS calcd. for C17H14NO2F6Br 458.0190 [M+H]+, found: 458.0199.
Workup
- extractionthe mixture was extracted with methylene chloride
- washThe organic layer was washed with brine and water
- dry with materialdried over anhydrous MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-3240cc2589a7437295e0cf47d765f95a
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476057B1
Reaction notes
Loading…