Bromoacetyl bromide → 3-Chloro-2-(bromoacetamido)benzoic Acid

HRID 1599814Notes

Reaction equation

HRID 1599814 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12][CH2:13][C:14](Br)=[O:15]>CN(C=O)C.O1CCOCC1>[Br:12][CH2:13][C:14]([NH:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 189292153-Chloro-2-(bromoacetamido)benzoic AcidYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-3-chlorobenzoic acid (7.0 g, 0.041 mol) in anhydrous DMF (20 mL) and anhydrous dioxane (20 mL) was cooled to 0° C. in a 250 mL 3-necked flask which was fitted with a magnetic stirring bar and a constant additional funnel. Bromoacetyl bromide was added dropwise over a 27 min period while keeping the internal temperature between 0° C. and 2° C. After the addition was complete, the ice-bath was removed and stirring was continued for 4 h. The reaction mixture was cooled using an ice-bath, water (100 mL) was added, and then the yellow precipitate which formed was filtered. The filtered solid was washed with water and then dried in a vacuum oven for 2 days, yielding 7.7 g (65%) of the title compound as a light yellow crystals: mp 173°-175° C.; 1H NMR (CD3OD) δ7.88 (dd, 1H, J=1.6, J=6), 7.68 (dd, 1H, J=1.2, J=6.8), 7.39 (t, 1H, J=8), 6.6 (bs, 1H, NH), 4.06 (s, 2H); 13C NMR (CD3OD) δ176.57, 168.38, 134.84, 134.40, 131.95, 130.53, 129.15, 129.05, 28.66; MS (EI, m/z) 293 (M+).

Workup

  1. customwas fitted with a magnetic stirring bar and a constant additional funnel
  2. customthe internal temperature between 0° C. and 2° C
  3. additionAfter the addition
  4. customthe ice-bath was removed
  5. temperatureThe reaction mixture was cooled
  6. additionwater (100 mL) was added
  7. customthe yellow precipitate which formed
  8. filtrationwas filtered
  9. washThe filtered solid was washed with water
  10. customdried in a vacuum oven for 2 days

Sources & evidence

ORD record
ord-541f59139dcd4f8993f73e49c3a006d1
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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