Carbon tetrabromide → HCID 67983924, compound

HRID 1748186Notes

Reaction equation

HRID 1748186 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:5]=2[CH2:16]O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:16][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67983767HCID 67983767, compound

Product 1

HCID 67983924HCID 67983924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 100 mL round bottom flask was placed (5-cyclopropyl-3-(o-tolyl)isoxazol-4-yl)methanol (1.86 g, 8.11 mmol), triphenylphosphine (3.50 g, 12.2 mmol, 1.5 equiv) and dichloromethane (50 mL). The mixture was stirred until completely dissolved, and then slowly cannulated dropwise into a stirring solution of carbon tetrabromide (4.00 g, 12.2 mmol, 1.5 eq) in dichloromethane (20 mL). The solution was stirred for one hour and the solvent was then evaporated in vacuo. The crude residue was purified by silica gel chromatography using a 0-50% gradient of ethyl acetate/hexanes. The desired product was obtained as a yellow oil. MS m/z 292.0/294.0 (M+1, Br79/Br81 isotope pattern).

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. dissolutionuntil completely dissolved
  3. stirringThe solution was stirred for one hour
  4. customthe solvent was then evaporated in vacuo
  5. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-aca8ede0afbf488cad32a0b585e011e9
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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