Diethyl Ether → 1,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-ol

HRID 599799Notes

Reaction equation

HRID 599799 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([OH:21])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)=O.B.C1COCC1.[NH4+].[Cl-].CCOCC>C1COCC1>[F:14][C:13]([F:15])([F:16])[C:12]([C:9]1[CH:8]=[CH:7][C:6]([NH:5][CH2:3][C:2]([F:1])([F:23])[F:22])=[CH:11][CH:10]=1)([OH:21])[C:17]([F:20])([F:19])[F:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 16371562,2,2-trifluoro-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]acetamideHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 4479111,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-olYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.2 g (11.8 mmol) of 2,2,2-trifluoro-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-acetamide in 30 mL of THF was treated with 24.2 mL of a 1M BH3.THF-complex solution in THF. The mixture was stirred for 72 hours at RT and then refluxed for 2 hours. After cooling to RT, the mixture was distributed between a saturated aqueous solution of NH4Cl and Et2O. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silicagel with n-heptane/EtOAc 4:1 yielded 3.0 g (74%) of 1,1,1,3,3,3-hexafluoro-2-[4-(2,2,2-trifluoro-ethylamino)-phenyl]-propan-2-ol, light brown oil, MS: 342 (MH+).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureAfter cooling to RT
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-b6b9e6624e8149e7836dabbf728ac548
Source dataset
uspto-grants-2011_03
Patent number
US07897815B2

Reaction notes

Loading…