Phosphorus tribromide → HCID 89656327, compound

HRID 930919Notes

Reaction equation

HRID 930919 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:17]O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].P(Br)(Br)[Br:20].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:17][Br:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 89656502HCID 89656502, compound

Product 1

HCID 89656327HCID 89656327, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 287b (3.70 g, 11.74 mmol) in dichloromethane (20 mL) was added phosphorus tribromide (1.11 mL, 11.7 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 hours, and poured into ice water. The pH was adjusted to basic by the careful addition of saturated aqueous sodium bicarbonate and the mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (4.15 g, 93%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3805940aa1f147029c310bb74b4ae79d
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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