Water → 2-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

HRID 84428Notes

Reaction equation

HRID 84428 reaction equation
[S:1]1[C:10]2[C:9]3[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:8]=3[O:7][CH2:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[Br:17]N1C(=O)CCC1=O.O>ClCCl.C(O)(=O)C>[Br:17][C:2]1[S:1][C:10]2[C:9]3[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:8]=3[O:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 568341544,5-Dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

Product 1

HCID 568341552-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile (4.58 g) in dichloromethane (30 mL) and acetic acid (30 mL) was added N-bromosuccinimide (3.95 g) and the reaction stirred at room temperature for 16 h. Water (100 mL) was then added and the solid collected by filtration and air-dried to give 2-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile.

Workup

  1. filtrationthe solid collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-71a2d7e84ecd40ac82e2c9eee2b94c6b
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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