Phosphorus tribromide → HCID 59589356, compound

HRID 630006Notes

Reaction equation

HRID 630006 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12]O.P(Br)(Br)[Br:15]>ClCCl>[Br:15][CH2:12][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 224397(4-Chloroquinolin-3-yl)methanol

Product 1

HCID 59589356HCID 59589356, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chloroquinolin-3-yl)methanol (1.0 mg, 5.2 mmol) in anhydrous dichloromethane (50 mL) was added dropwise phosphorus tribromide (1.0 mL, 11.2 mmol). The mixture was stirred at room temperature for 3 hours. Dichloromethane was evaporated. Water (20 mL) was added. The mixture was treated slowly with a saturated aqueous sodium bicarbonate solution. The mixture was extracted with dichloromethane (2×30 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 3-(bromomethyl)-4-chloroquinoline (982 mg, 74% yield). The product was used without further purification.

Workup

  1. customDichloromethane was evaporated
  2. additionWater (20 mL) was added
  3. additionThe mixture was treated slowly with a saturated aqueous sodium bicarbonate solution
  4. extractionThe mixture was extracted with dichloromethane (2×30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5b648e3954a94ba79282b46cd43ede2c
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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