1,3-Dibromopropane → HCID 59700576, compound

HRID 901832Notes

Reaction equation

HRID 901832 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:15][CH2:14][CH2:13][Br:12])[CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 10340Sodium CarbonateHCID 144229537-Fluoro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 59700576HCID 59700576, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine (1.3 g, 1 eq, 8.49 mmol) obtained in step (iii) above, 1,3-dibromo propane (8.6 ml, 10 eq, 84.9 mmol) and anhydrous sodium carbonate (2.7 g, 3 eq, 25.4 mmol) in dry DMF (85 ml) was heated at 70° C. for 16 h. The reaction 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 (1.1 g, yield 47%) as viscous oil.

Workup

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

Sources & evidence

ORD record
ord-2a01adcf746d4d7191aec9feb880a20a
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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