Hydrogen Bromide → 3-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine

HRID 271457Notes

Reaction equation

HRID 271457 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=1.[BrH:14]>>[Br:14][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:10]([F:13])([F:12])[F:11])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol

Product 1

HCID 598348213-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridineYield 71%

Conditions

Temperature
135 °C

Procedure

A mixture of (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (1.677 g, 8.77 mmol, 76% pure) in 48% aq. HBr (10 mL) was heated to reflux (oil bath temperature, 135° C.) for 24 h. The volatile components of the resulting biphasic mixture were distilled under vacuum to remove most of the hydrogen bromide (sodium hydroxide trap). The residue was partitioned between 2:1 EtOAc/THF and water (at pH 3) and the organic phase was dried (MgSO4), filtered and evaporated. The solid residue was re-evaporated after addition of dichloromethane/hexanes to obtain the title compound as a tan solid, 1.19 g, 71% yield (based on the purity of the starting material). HPLC/MS: retention time=2.15 min, [M+H]30 =254.

Workup

  1. temperaturewas heated
  2. distillationThe volatile components of the resulting biphasic mixture were distilled under vacuum
  3. customto remove most of the hydrogen bromide (sodium hydroxide trap)
  4. customThe residue was partitioned between 2:1 EtOAc/THF and water (at pH 3)
  5. dry with materialthe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was re-evaporated
  9. additionafter addition of dichloromethane/hexanes

Sources & evidence

ORD record
ord-e6e5ef9fbfeb452595567ab337decb6b
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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