Carbon tetrabromide → 4-(3-bromopropyl)-1-methyl-1H-pyrazole

HRID 220450Notes

Reaction equation

HRID 220450 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9]O)[CH:4]=[N:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:31]>C(Cl)(Cl)Cl>[Br:31][CH2:9][CH2:8][CH2:7][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 188014053-(1-Methyl-1H-pyrazol-4-yl)propan-1-ol

Product 1

HCID 457914634-(3-bromopropyl)-1-methyl-1H-pyrazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 3-(1-methyl-1H-pyrazol-4-yl)-propan-1-ol (0.250 g, 1.783 mmol) in dry chloroform (15 mL). Add PS-triphenylphosphine resin (1.824 g, 3.923 mmol) and carbon tetrabromide (0.650 g, 1.961 mmol). Stir at room temperature under nitrogen for 3 hr. Filter reaction over paper with DCM. Concentrate filtrate in vacuo to obtain the title preparation (0.362 g, 100% yield). GC-MS (m/z): 202/204(M+), 95.

Workup

  1. filtrationFilter
  2. customreaction over paper with DCM
  3. customConcentrate filtrate in vacuo to obtain the title
  4. custompreparation (0.362 g, 100% yield)

Sources & evidence

ORD record
ord-af70f8d553b64befa29b4612cb509cd2
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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