Bromine → 1522241-39-9

HRID 595229Notes

Reaction equation

HRID 595229 reaction equation
[Br:1]Br.[CH2:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1C=CC=CC=1)[CH2:4]C=C>C(Cl)Cl.O>[Br:1][CH2:11][CH:10]1[O:9][C:8](=[O:17])[NH:7][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 24408BromineHCID 14688338Benzyl but-3-en-1-ylcarbamate

Product 1

HCID 1182088701522241-39-9

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (11 g, 68 mmol) was added to a mixture of benzyl but-3-en-1-ylcarbamate (7 g, 34 mmol) in DCM at room temperature under N2. The mixture was stirred at room temperature for 4 hours. The mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford 6-(bromomethyl)-1,3-oxazinan-2-one. 1H NMR (400 MHz, CDCl3) δ 6.14 (s, 1H), 4.49-4.45 (m, 1H), 3.59-3.56 (m, 1H), 3.46-3.39 (m, 3H), 2.24-2.20 (m, 1H), 1.95-1.89 (m, 1H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-69dfa9a436d94c1cb098a91b0bcfacb6
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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