Bromoacetyl bromide → HCID 10731139, compound

HRID 1490278Notes

Reaction equation

HRID 1490278 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F: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.O>[Br:12][CH2:13][C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

6

Reactant 2

HCID 61147Bromoacetyl bromideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 10731139HCID 10731139, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-5-fluorobenzoic acid (15 g, 96.6 mmol) in dry DMF (35 mL) and dioxane (35 mL) was cooled to 0° C. Bromoacetylbromide (8.43 mL, 96.6 mmol) was added dropwise at 0° C. over a 40 min period, and the reaction mixture was left overnight at room temperature. The reaction mixture was cooled to 0° C., and diluted slowly with water (300 mL). The precipitate which formed was collected washed with 5% HBr (50 mL) and water, and dried, to afford 25.43 g (95.1%) of the title compound as a white solid, mp 191.2°-191.8° C.; 1H NMR (acetone-d6) δ 11.60 (s, 1H), 8.71 (dd, J=5.2, J=9.2, 1H), 7.80 (dd, J=3.2, J=9.6, 1H), 7.48-7.43 (m, 1H), 4.18 (s, 2H); 13C NMR (acetone-d6) δ 168.80, 165.71, 158.37 (d, J=241.9), 138.56, 122.78 (d, J=7.8), 122.70, 122.06 (d, J=21.9), 117.98 (d, J=24.0), 30.45; MS (EI, m/z) 277 (M+).

Workup

  1. customThe precipitate which formed
  2. customwas collected
  3. washwashed with 5% HBr (50 mL) and water
  4. customdried

Sources & evidence

ORD record
ord-1fc4b1d95a9d44c9876095a92cd8c3d5
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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