Water → HCID 15491246, compound

HRID 2374227Notes

Reaction equation

HRID 2374227 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[CH2:17]O.P(Br)(Br)[Br:20].O>C(OCC)(=O)C>[Br:20][CH2:17][C:3]1[CH:4]=[C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[O:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 15491245HCID 15491245, compound

Product 1

HCID 15491246HCID 15491246, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

12 g of the N-(4-chloro-3-hydroxymethylphenyl)-2-methyl-3-furancarboxamide prepared in Step 5 above, was dissolved in 180 mL ethyl acetate. 1.8 mL of phosphorus tribromide was then added. The resultant mixture was stirred for 90 minutes at room temperature. 100 mL of water was then added to the mixture. The resultant organic phase was separated, washed with water, aqueous sodium bicarbonate solution and water, and then dried over magnesium sulfate. The solvent was evaporated off to produce 12.97 g of N-(3-bromomethyl-4-chlorophenyl)-2-methyl-3-furancarboxamide as a solid.

Workup

  1. customThe resultant organic phase was separated
  2. washwashed with water, aqueous sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-30e64d734a854e429ff97b4ea019e6aa
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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