Dimethylformamide → 3-Chloro-2-(bromoacetamido)benzoic Acid

HRID 1490291Notes

Reaction equation

HRID 1490291 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].CN(C=O)C.O1CCOCC1.[Br:23][CH2:24][C:25](Br)=[O:26]>O>[Cl:11][C:10]1[C:2]([NH:1][C:25](=[O:26])[CH2:24][Br:23])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 61147Bromoacetyl bromideHCID 808072-Amino-3-chlorobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-3-chlorobenzoic acid (7 g, 0.041 mol), anhydrous DMF (20 mL) and anhydrous dioxane (20 mL) was cooled to 0° C. in a 250 mL 3-necked flask, fitted with a magnetic stirrer and constant additional funnel. Bromoacetyl bromide was added dropwise over a 27 min period, keeping the internal temperature between 0° to 2° C. After the addition was complete, the solution was allowed to warm to room temperature and stirring was continued for 4 hours. The reaction mixture was cooled in an ice-bath and diluted with water (100 mL). The resulting yellow precipitate was filtered, washed with water and dried in vacuum oven for 2 days, affording 7.7 g (65%) of the title compound as a light yellow crystals, mp 173°-175° C.; 1H NMR (CD3OD) 7.88 (dd, 1H, J=1.6, J=6), 7.68 (dd, 1H, J=1.2, J=6.8), 7.39 (t, 1H, J=8); 13C NMR (CD3OD) δ 176.37, 168.38, 134.84, 134.40, 131.95, 130.53, 129.15, 129.05, 28.66; MS (EI, m/z) 293 (M+).

Workup

  1. customfitted with a magnetic stirrer and constant additional funnel
  2. custombetween 0° to 2° C
  3. additionAfter the addition
  4. temperatureThe reaction mixture was cooled in an ice-bath
  5. filtrationThe resulting yellow precipitate was filtered
  6. washwashed with water
  7. customdried in vacuum oven for 2 days

Sources & evidence

ORD record
ord-35537ff0405c4b73a6e64364aa9d0084
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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