Carbon tetrabromide → 5-(1-Bromopropyl)-3-methylisoxazole

HRID 1048486Notes

Reaction equation

HRID 1048486 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7](O)[CH2:8][CH3:9])[O:4][N:3]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:12][CH:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 585732171-(3-Methylisoxazol-5-yl)propan-1-ol

Product 1

HCID 585731595-(1-Bromopropyl)-3-methylisoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-methylisoxazol-5-yl)propan-1-ol (0.589 g, 4.17 mmol) in 15 mL of THF was added CBr4 (1.730 g, 5.22 mmol) and triphenylphosphine (1.423 g, 5.42 mmol). The reaction mixture was stirred at room temperature for 3 h. The solid was filtered off, and washed with THF. The filtrate was concentrated and residue was purified by chromatography on silica gel, eluting with 5 to 30% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=204.2 (M+1).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customresidue was purified by chromatography on silica gel
  5. washeluting with 5 to 30% EtOAc/hexane

Sources & evidence

ORD record
ord-70619d2613f74153a9176be870689a9a
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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