Water → HCID 18929216, compound

HRID 1599813Notes

Reaction equation

HRID 1599813 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[Br:12][CH2:13][C:14](Br)=[O:15].O>CN(C=O)C.O1CCOCC1>[Br:12][CH2:13][C:14]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

6

Reactant 3

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 5211422-Amino-6-fluorobenzoic acid

Product 1

HCID 18929216HCID 18929216, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-6-fluorobenzoic acid (8.0 g, 0.052 mol) in anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) at 0° C. in a 250 mL 3-necked flask fitted with a constant additional funnel was added, dropwise, bromoacetyl bromide (10.4 g, 100 mol%) while keeping the internal temperature between 0° C. and 2° C. After the addition was completed (~30 min), the reaction mixture was stirred at rt overnight. Water (100 mL) was added, and the light crystalline compound which precipitated was filtered, washed sequentially with 5% HBr and water, and then dried in a vacuum oven at 40°-45° C., affording 9.5 g (67%) of the title compound: mp 168.9°-170.3° C.; 1H NMR (DMSO-d6) δ13.80 (bs, 1H, OH), 10.60 (s, 1H, NH), 7.69 (d, 1H, J=8.4), 7.54 (dt, 1H, J=8.4, J=10.4), 7.13-7.08 (m, 1H), 4.16 (s, 2H); 13C NMR (DMSO-d6) δ165.22 (d, J=32.4, C=O), 160.18 (d, J=251), 137.83, 132.69 (d, J=10.0), 118.58, 118.20, 112.18 (d, J=22.9), 30.04; MS (EI, m/z) 275 (M+). HRMS (EI) calcd for C9H7NO3FBr 274.9593, found 274.9595. Anal. Calcd for C9H7NO3FBr: C, 39.16; H, 2.56; N, 5.08. Found: C, 38.96; H, 2.48; N, 5.07.

Workup

  1. additionwas added
  2. customthe internal temperature between 0° C. and 2° C
  3. additionAfter the addition
  4. custom(~30 min)
  5. customthe light crystalline compound which precipitated
  6. filtrationwas filtered
  7. washwashed sequentially with 5% HBr and water
  8. customdried in a vacuum oven at 40°-45° C.

Sources & evidence

ORD record
ord-f2d0cc17195145579c396495d7f19e8f
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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