Bromotrimethylsilane → 6-(bromomethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2246939Notes

Reaction equation

HRID 2246939 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:7]=2[CH:18]=1.[Br:19][Si](C)(C)C>C(Cl)(Cl)Cl>[Br:19][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:7]=2[CH:18]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 534011966-Hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 468352246-(bromomethyl)-4-(3-methoxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 74.0 g of 6-hydroxymethyl-4-(3-methoxy-propyl)-4H-benzo[1,4]oxazin-3-one (from example 1 g) in 600 ml of chloroform are added 58 ml of bromotrimethylsilane at room temperature. The reaction mixture is stirred for 30 minutes and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as an off white solid. Rf=0.46 (EtOAc-heptane 1:1); Rt=4.03.

Workup

  1. customat room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-b65de117807541049b7146a8232489c4
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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