Dimethylformamide → HCID 10731139, compound

HRID 1599812Notes

Reaction equation

HRID 1599812 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].CN(C=O)C.O1CCOCC1.[Br:23][CH2:24][C:25](Br)=[O:26]>O>[Br:23][CH2:24][C:25]([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:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 61147Bromoacetyl bromideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 10731139HCID 10731139, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 2-amino-5-fluorobenzoic acid (15.0 g, 96.6 mmol) in a mixture of dry DMF (35 mL) and dioxane (35 mL) was added, dropwise, bromoacetylbromide (8.43 mL, 96.6 mmol) at 0° C. over a 40 min period, and then the reaction mixture was allowed to come to room temperature overnight. The reaction mixture was cooled to 0° C., water (300 mL) was added slowly, and then the precipitate which formed was collected and washed with 5% HBr (50 mL) and water. After drying, 25.43 g (95.1%) of the title compound was obtained as a white solid: mp 191.2°-191.8° C.; 1H NMR (acetone-d6) δ11.60 (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) δ168.80, 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+). HRMS (EI) calcd for C9H7NO3FBr 274.9593, found 274.9594.

Workup

  1. additionwas added
  2. customthe precipitate which formed
  3. customwas collected
  4. washwashed with 5% HBr (50 mL) and water
  5. customAfter drying

Sources & evidence

ORD record
ord-9d12abdd3b244889aab6dc621151ecad
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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