Bromoacetyl bromide → HCID 18929201, compound

HRID 1599817Notes

Reaction equation

HRID 1599817 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[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[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 18929201HCID 18929201, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-6-chlorobenzoic acid (10.0 g, 0.06 mol) in anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) was cooled to 0° C. in 300 mL 3-necked flask fitted with a magnetic stirring bar and constant additional funnel. Bromoacetyl bromide was added dropwise over a 20-25 min period, while maintaining the internal temperature between 0° C. to 1° C. After the addition was completed, the ice-bath was removed and stirring was continued for 20 h. The reaction mixture was cooled in an ice-bath, water (150 mL) was added, and then the yellow crystalline product which formed was filtered and washed sequentially with 5% HBr solution (50 mL) and water (50 mL). After drying in a vacuum oven (20 h, 40°-45° C.), 5.0 g (30%) of the title compound was obtained: mp 133°-135° C. (dec.); 1H NMR (CD3OD) δ7.70 (d, 1H, J=8), 7.43 (t, 1H, J=8.4), 7.35 (d, 1H, J=8), 4.05 (s, 2H); 13C NMR (CD3OD) δ168.19, 167.84, 137.24, 133.31, 132.85, 132.08, 128.78, 128.21, 124.20, 29.21; MS (EI, m/z) 293 (M+)

Workup

  1. customfitted with a magnetic stirring bar and constant additional funnel
  2. temperaturewhile maintaining the internal temperature between 0° C. to 1° C
  3. additionAfter the addition
  4. customthe ice-bath was removed
  5. temperatureThe reaction mixture was cooled in an ice-bath
  6. additionwater (150 mL) was added
  7. customthe yellow crystalline product which formed
  8. filtrationwas filtered
  9. washwashed sequentially with 5% HBr solution (50 mL) and water (50 mL)
  10. customAfter drying in a vacuum oven (20 h, 40°-45° C.)

Sources & evidence

ORD record
ord-907d45d708ec40c697fff59ff816163d
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

Loading…