Dichloromethane → HCID 66646046, compound

HRID 1907372Notes

Reaction equation

HRID 1907372 reaction equation
ClCCl.B(Br)(Br)Br.C[O:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[C:16](=[O:21])[NH:15][C:14]=2[CH:22]=1>O>[OH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][C:17]([CH3:19])([CH3:20])[C:16](=[O:21])[NH:15][C:14]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 66645913HCID 66645913, compound

Product 1

HCID 66646046HCID 66646046, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dichloromethane solution (36 ml) of 2M boron tribromide was added dropwise to a dichloromethane solution of 6-methoxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (5.0 g, 26 mmol) under ice cooling and the mixture was stirred overnight. Water was added to the reaction solution to decompose the reagents excessively present. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1). The purified product was concentrated to dryness under reduced pressure to obtain 6-hydroxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (4.02 g) as white powder.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c1f92b2557ce4d7c821f9ab89183963b
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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