N-bromobutanimide → 2-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 1807711Notes

Reaction equation

HRID 1807711 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:18][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:4]([F:6])([F:5])[F:7])[C:2]([F:16])([F:17])[F:1])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 748292-(p-Tolyl)hexafluoroisopropanol

Product 1

HCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olYield 105.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-p-tolylpropan-2-ol (387 mmol, 100 g) was dissolved in carbon tetrachloride (400 mL) and N-bromosuccinimide (387 mmol, 68.9 g) was added in one portion followed by 2,2′-azobis(isobutyronitrile) (0.387 mmol, 0.064 g). The reaction was stirred at reflux for 4 hours, filtered through dicalite and the filtrate was evaporated to leave crude oil. The crude oil was triturated with diethyl ether, the solid obtained was filtered off and the filtrate taken to dryness (3 times) to yield the title compound as an oil (138 g). 1H NMR (CDCl3, 400 MHz): δ 4.49 (2H, s), 7.49 (2H, d), 7.69 (2H, d)

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationfiltered through dicalite
  3. customthe filtrate was evaporated
  4. customto leave crude oil
  5. customThe crude oil was triturated with diethyl ether
  6. customthe solid obtained
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-4c76a950b323462fa5f052aba506ea3f
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…