Water → 4-(Bromomethyl)-5-iodo-2-(trifluoromethyl)pyridine

HRID 604640Notes

Reaction equation

HRID 604640 reaction equation
[I:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[C:2]([I:1])=[CH:7][N:6]=[C:5]([C:8]([F:11])([F:9])[F:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 670577315-Iodo-4-methyl-2-(trifluoromethyl)pyridine

Product 1

HCID 670577364-(Bromomethyl)-5-iodo-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-iodo-4-methyl-2-(trifluoromethyl)pyridine (39.1 mg, 0.136 mmol), N-bromosuccinimide (29.1 mg, 0.163 mmol), and benzoyl peroxide (3.3 mg, 0.0136 mmol) in CCl4 (1 mL) was heated at reflux under N2 overnight. Water was added and the mixture was extracted with CH2Cl2 (3×20 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 1-5% EtOAc in hexanes gradient) to afford 4-(bromomethyl)-5-iodo-2-(trifluoromethyl)pyridine. Rf=0.41 (10% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 9.03 (s, 1H); 7.76 (s, 1H); 4.51 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 overnight
  3. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash chromatography (Si, 12×160 mm, 1-5% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-e72698d940a74ef789c99beb570d7183
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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