Pyridine → HCID 54080281, compound

HRID 2061380Notes

Reaction equation

HRID 2061380 reaction equation
[CH:1]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.P(Br)(Br)[Br:30]>C1(C)C=CC=CC=1>[Br:30][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 53721633HCID 53721633, compound

Product 1

HCID 54080281HCID 54080281, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

(4-(Benzhydryloxy)phenyl)methanol (500 mg, 1.72 mmol) was dissolved in toluene (20 ml) and pyridine (139 uL, 1.72 mmol) was added. The solution was cooled to 0° C. PBr3 (163 uL, 1.72 mmol) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 1 h. It was then washed with saturated K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo to obtain ((4-(bromomethyl)phenoxy)methylene)dibenzene as an oil, (450 mg, 74%). This intermediate was used in the following reaction.

Workup

  1. washIt was then washed with saturated K2CO3 solution
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe EtOAc layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated off in-vacuo

Sources & evidence

ORD record
ord-9304ee61e6c3408484f37e1fa2c5fc5a
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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