Acetic Acid → 2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

HRID 627898Notes

Reaction equation

HRID 627898 reaction equation
[S:1]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.C(O)(=O)C.[Br:19]N1C(=O)CCC1=O>ClCCl>[Br:19][C:2]1[S:1][C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 579001554,5-Dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 579002002-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine (440 mg, 2.2 mmol) and acetic acid (10 ml) in dichloromethane (10 ml) at 0° C., was added N-bromosuccinimide in portions. Reaction mixture was stirred for 18 hours, allowing solution to raise to room temperature before being concentrated in-vacuo. Residue was dissolved in ethyl acetate and sat. sodium carbonate solution. Organic phase was washed with water and brine, dried (Na2SO4) and concentrated in-vacuo to give 2-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine.

Workup

  1. customReaction mixture
  2. concentrationbefore being concentrated in-vacuo
  3. dissolutionResidue was dissolved in ethyl acetate
  4. washOrganic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-6da35591b3084423806dae12eea0b292
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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