1,3-Dibromopropane → HCID 59700589, compound

HRID 901835Notes

Reaction equation

HRID 901835 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[NH:4][CH2:3]1.[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[N:4]([CH2:16][CH2:15][CH2:14][Br:13])[CH2:3]1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 10340Sodium CarbonateHCID 54595313515861-53-7

Product 1

HCID 59700589HCID 59700589, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-methyl-7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine (4.3 g, 1 eq, 25.74 mmol) obtained in step (iii) above, 1,3-dibromo propane (26.1 ml, 10 eq, 257 mmol) and anhydrous sodium carbonate (8.2 g, 3 eq, 77.2 mmol) in dry DMF (260 ml) was heated at 70° C. for 16 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue was chromatographed using ethyl acetate and hexane to afford the title compound (3.5 g, yield 48%) as viscous oil.

Workup

  1. washwashed with water and brine
  2. customThe residue was chromatographed

Sources & evidence

ORD record
ord-8fb0df49fdfe45d8a47c099797afeb7d
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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