Bromoacetyl bromide → HCID 18929214, compound

HRID 1599819Notes

Reaction equation

HRID 1599819 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[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[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 18929214HCID 18929214, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-bromobenzoic acid (11.2 g, 0.052 mol) in anhydrous DMF (40 mL) and anhydrous dioxane (40 mL) was added, dropwise, bromoacetyl bromide while keeping the internal temperature between 0° C. and 5° C. After the addition was completed (~25 min), the ice-bath was removed and the mixture was stirred for 20 h at rt. The reaction mixture was cooled in an ice-bath, water was added (100 mL), and then the mixture was poured into ice water. The precipitate which formed was filtered, washed with water, and then dried in a vacuum oven for 20 h at 40°-45° C., affording 9.9 g (57%) of the title compound: mp 203°-204° C.; 1H NMR (CDCl3) δ11.67 (s, 1H, NH), 8.64 (d, 1H, J=8.8), 8.55 (d, 1H, J=2.4), 7.71 (dd, 1H, J=2, J=6.8), 3.72 (s, 2H ); 13C NMR (CDCl3): 200.55, 138.06, 134.22, 134.20, 122.06, 107.46. 67.08; MS (EI, m/z) 337 (M+). HRMS (EI) calcd for C9H7NO3Br2 334.8792, found 334.8791.

Workup

  1. customthe internal temperature between 0° C. and 5° C
  2. additionAfter the addition
  3. custom(~25 min)
  4. customthe ice-bath was removed
  5. temperatureThe reaction mixture was cooled in an ice-bath
  6. additionwater was added (100 mL)
  7. additionthe mixture was poured into ice water
  8. customThe precipitate which formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried in a vacuum oven for 20 h at 40°-45° C.

Sources & evidence

ORD record
ord-e12fcb0399444242b85d41ea13e00540
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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