Bromine → HCID 18442663, compound

HRID 915902Notes

Reaction equation

HRID 915902 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1([C:14]([F:17])([F:16])[F:15])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:13])[O:4]1.C([O-])(=O)C.[K+].[Br:25]Br>C(O)(=O)C.[Cl-].[Na+].O>[Br:25][C:10]1[CH:11]=[CH:12][C:7]2[NH:6][C:5](=[O:13])[O:4][C:3]([C:14]([F:17])([F:16])[F:15])([C:2]([F:1])([F:18])[F:19])[C:8]=2[CH:9]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 18442662HCID 18442662, compound

Product 1

HCID 18442663HCID 18442663, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4,4-bis(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (0.50 g, 1.75 mmol) in glacial acetic acid (6 mL) buffered with potassium acetate (0.52 g, 5.25 mmol) was added bromine (0.28 g, 1.75 mmol). The reaction was stirred 30 minutes and poured into brine (30 mL), and extracted with ethyl acetate several times. The organic layer was dried over magnesium sulfate and concentrated. Flash column separation using 10% ethyl acetate/hexane gave 0.36 g of 6-bromo-4,4-bis(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white solid (57%). 1H NMR (DMSO-d6): δ 11.57 (s, 1H), 7.85 (dd, J=8.7, 2.2 Hz, 1H), 7.60 (s, 1H), 7.08 (d, J=8.7 Hz, 1H). MS (ESI) m/z 362/364 ([M+H]+); HRMS: calcd for C10H4BrF6NO2, 362.9330; found (ESI_FT), 363.93994.

Workup

  1. extractionextracted with ethyl acetate several times
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customFlash column separation

Sources & evidence

ORD record
ord-33a715779ccf48fdb4c2b6995bb5909a
Source dataset
uspto-grants-2007_09
Patent number
US07268149B2

Reaction notes

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