N-bromobutanimide → 2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrile

HRID 2385647Notes

Reaction equation

HRID 2385647 reaction equation
[S:1]1[C:5]2[C:6]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:24][C:2]1[S:1][C:5]2[C:6]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 582037704,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrile

Product 1

HCID 582038742-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrileYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrile (240 mg, 1.05 mmol) in 3 ml of DMF was treated with NBS (206 mg, 1.16 mmol) at room temperature for 15 hours. The reaction mixture was diluted with a large volume of EtOAc and the organic was washed with water and saline and concentrated in vacuo to a solid. This residue was filtered onto celite and purified by MPLC on a 14 gram silica column, eluting with 20-80% EtOAc/heptanes to give 200 mg (62%) of 2-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrile as a white powder in high purity as determined by LC/MS.

Workup

  1. washthe organic was washed with water and saline
  2. concentrationconcentrated in vacuo to a solid
  3. filtrationThis residue was filtered onto celite
  4. custompurified by MPLC on a 14 gram silica column
  5. washeluting with 20-80% EtOAc/heptanes

Sources & evidence

ORD record
ord-029cc35758924001a25d80a3043cb15e
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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