Phosphorus tribromide → HCID 67112138, compound

HRID 594993Notes

Reaction equation

HRID 594993 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([NH2:10])=[O:9].P(Br)(Br)[Br:15]>ClCCl>[Br:15][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([NH2:10])=[O:9]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 9273882-[3-(Hydroxymethyl)phenoxy]acetamide

Product 1

HCID 67112138HCID 67112138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-(hydroxymethyl)phenoxy)acetamide (320 mg, 1.76 mmol) was suspended in dichloromethane (12 mL) and the suspension cooled to 0° C. (ice bath). Phosphorus tribromide (1.5 eq) was added slowly and the reaction allowed to warm to rt. After stirring for 18 h the reaction was quenched by addition of NaHCO3 (sat., aq). The product was extracted with dichloromethane, dried (Na2SO4), filtered and concentrated in vacuo to afford 2-(3-(bromomethyl)phenoxy)acetamide as a white solid.

Workup

  1. temperatureto warm to rt
  2. customwas quenched by addition of NaHCO3 (sat., aq)
  3. extractionThe product was extracted with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3457c9591d86463eab43a351505e0c1c
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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