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

HRID 932172Notes

Reaction equation

HRID 932172 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-86c4d6f88874492c8aeb34b80e129ee1
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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