Chloroacetyl chloride → 7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1861867Notes

Reaction equation

HRID 1861867 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C([O-])(O)=O.[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>C(C(C)=O)C(C)C.O.C(OCC)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:17](=[O:18])[CH2:16][O:9][C:3]=2[CH:4]=1

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 143206052-Amino-5-bromophenol

Product 1

HCID 143051127-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part 2. A solution of 2-amino-5-bromophenol (2.53 g, 18.2 mmol, 1.0 equiv) in 15 mL of isobutylmethyl ketone and 15 mL of water was cooled to 0° C., NaHCO3 (3.67 g, 2.4 equiv) and then chloroacetyl chloride (2.36 g, 1.67 mL, 1.15 equiv) were added. The mixture was heated to reflux overnight, then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and concentrated in vacuo. Flash chromatography on silica gel gave 7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one in 77% yield. LRMS found for C9H10NO3 (M+H)+: 180.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f5dbcba51744ff89338a1c6f0f7949b
Source dataset
uspto-grants-2003_03
Patent number
US06534535B1

Reaction notes

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