Phosphorus tribromide → HCID 59603169, compound

HRID 2061355Notes

Reaction equation

HRID 2061355 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11]O)=[CH:8][C:7]=2[CH:13]=1.P(Br)(Br)[Br:15]>C1(C)C=CC=CC=1>[Br:15][CH2:11][C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:13][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 15161064(5-Methoxy-1-benzofuran-2-yl)methanol

Product 1

HCID 59603169HCID 59603169, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 25 (40 mg, 0.22 mmol) was dissolved in toluene (5 mL) and the solution was cooled to 0° C. PBr3 (21 μL, 0.22 mmol) was added dropwise over 10 min. The reaction mixture was then brought up to room temperature and stirred for 1 h. The solvent was evaporated off in-vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give 26 (40 mg, 74%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 7.39 (1H, d, J=8.90 Hz, H-7), 7.01 (1H, d, J=2.55, H-4), 6.94 (1H, dd, J=6.35 & 2.60, H-6), 6.72 (1H, s, H-3), 4.61 (2H, s, 2-CH2), 3.86 (3H, s, OCH3).

Workup

  1. customwas then brought up to room temperature
  2. customThe solvent was evaporated off in-vacuo
  3. custompurified by flash chromatography
  4. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-18de59029b52485cab72b893be432576
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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