Carbon tetrabromide → 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole

HRID 1772929Notes

Reaction equation

HRID 1772929 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[CH3:6][N:7]1[C:11](CO)=[CH:10][C:9]([CH3:14])=[N:8]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:5][CH2:1][C:11]1[N:7]([CH3:6])[N:8]=[C:9]([CH3:14])[CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2776363(1,3-dimethyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 534165735-(Bromomethyl)-1,3-dimethyl-1H-pyrazoleYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

CBr4 (4.7 g, 14.2 mmol) was added to a solution of (1,3-dimethyl-1H-pyrazol-5-yl)methanol (1.2 g, 9.5 mmol) and triphenylphosphine (3.7 g, 14.2 mmol) in THF (20 mL) at 0° C. and the resulting mixture was stirred for approximately 2 h at rt. After concentration in vacuo purification by column chromatography eluting with 2% EtOAc in hexane yielded the title compound (1.31 g, 6.93 mmol).

Workup

  1. concentrationAfter concentration
  2. customin vacuo purification by column chromatography
  3. washeluting with 2% EtOAc in hexane

Sources & evidence

ORD record
ord-adb57af00f0d4494848d5e1c0301e7e1
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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