Phosphorus tribromide → HCID 15155562, compound

HRID 2061348Notes

Reaction equation

HRID 2061348 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]O)=[CH:7][C:6]=2[CH:12]=1.P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[Br:14][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:12][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 23292349HCID 23292349, compound

Product 1

HCID 15155562HCID 15155562, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 14 (150 mg, 0.90 mmol) was dissolved in toluene (10 mL) and the solution was cooled to 0° C. PBr3 (102 μL, 1.08 mmol) was added dropwise over 15 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 15 (150 mg, 72%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 7.43 (1H, d, J=7.60 Hz, H-7), 7.21 (1H, t, J=8.10, H-4), 7.06 (1H, t, J=8.90, H-4), 6.75 (1H, s, H-3), 4.60 (2H, s, 2-CH2). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 113.08 (C-7), 112.08 (C-6), 106.87 (C-4), 106.34 (C-3), 60.42 (CH2—Br).

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-9c6a06b9dd1446b3aa29541e6cdd2fe8
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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