Acetic Acid → 3-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]amino]phenol

HRID 1060062Notes

Reaction equation

HRID 1060062 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:23])([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)[CH:11]([F:13])[F:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[F:9][C:10]([F:23])([O:14][C:15]1[CH:16]=[C:17]([CH2:18][NH:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH:20]=[CH:21][CH:22]=1)[CH:11]([F:12])[F:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115683-AminophenolHCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 109580163-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]amino]phenolYield 83.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

EX-20A) To a solution of 3-aminophenol (4.91 g, 45.0 mmol) and 3-(1,1,2,2-tetrafluoroethoxy)benzaldehyde (10.0 g, 45.0 mmol) in 100 mL of 1,2-dichloroethane was added sodium triacetoxyborohydride (14.28 g 67.5 mmol) and glacial acetic acid (2.7 mL, 47.3 mmol). The reaction mixture was stirred at room temperature for 6 h then quenched with water and extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and concentrated in vacuo to give 11.82 g (83%) of the desired 3-[[[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]methyl]amino]phenol product as a dark orange oil. 1H NMR (acetone-d6) δ 7.01-7.38 (m, 5H), 6.26-6.44 (m, 3H), 6.08 (t, 1H), 5.88 (tt, 1H), 4.34 (s, 2H).

Workup

  1. customthen quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a602e69753a49f5abf69ff377f081c6
Source dataset
uspto-grants-2003_02
Patent number
US06521607B1

Reaction notes

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