Sodium Bicarbonate → (2-Bromo-6-(trifluoromethyl)phenyl)methanol

HRID 1425940Notes

Reaction equation

HRID 1425940 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12]Br.C([O-])(O)=[O:15].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12][OH:15]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 227541361-Bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene

Product 1

HCID 68281421(2-Bromo-6-(trifluoromethyl)phenyl)methanolYield 98%

Procedure

To 1-bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene (CXXVIII) (7.51 g, 23.62 mmol) was added an aqueous saturated solution of NaHCO3 (400 mL). The reaction mixture was vigorously stirred and refluxed overnight. The reaction mixture consisted of an upper aqueous layer and a bottom oily layer, which solidified in an ice bath. The water layer was decanted and the solid was dissolved in EtOAc, dried over anhydrous MgSO4, filtrated and evaporated to dryness to give (2-bromo-6-(trifluoromethyl)phenyl)methanol (CXXIX) as an orange oil (5.49 g, 23.16 mmol, 98%). 1H NMR (DMSO-d6) δ ppm 4.67 (d, J=4 Hz, 2H), 5.23 (t, J=5 Hz, 1H), 7.43 (dd, J=8 Hz, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H); 19F NMR (DMSO-d6) δ ppm −56.33 (s, 3F); ESIMS found for C8H6BrF3O m/z 237.3 (M+H).

Workup

  1. temperaturerefluxed overnight
  2. customa bottom oily layer, which solidified in an ice bath
  3. customThe water layer was decanted
  4. dissolutionthe solid was dissolved in EtOAc
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltrated
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5cf1c259e5934ad89d5d2ef5cb210a04
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

Loading…