Carbon tetrabromide → HCID 86677486, compound

HRID 1621133Notes

Reaction equation

HRID 1621133 reaction equation
[CH3:1][C:2]1[C:3]([CH2:13]O)=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>ClCCl>[Br:35][CH2:13][C:3]1[C:2]([CH3:1])=[CH:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86677485HCID 86677485, compound

Product 1

HCID 86677486HCID 86677486, compoundYield 202%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-methyl-1-phenyl-1H-pyrazol-3-yl)methanol (158 mg, 0.84 mmol) and triphenylphosphine polymer bound (422 mg, 1.26 mmol) in dichloromethane (4.5 mL) was added carbon tetrabromide (416 mg, 1.26 mmol) at 0-5° C. The ice bath was removed after 15 min and the mixture was stirred at RT for 2 h. The mixture was filtered, washed with dichloromethane and the solvent was evaporated to give 426 mg crude material. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow oil (115 mg, 458 μmol, 38.3%).

Workup

  1. customThe ice bath was removed after 15 min
  2. filtrationThe mixture was filtered
  3. washwashed with dichloromethane
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-68dd9baf7fcb4cbaa8ab1b8c7d270567
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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