Acetic Anhydride → HCID 68892581, compound

HRID 2220202Notes

Reaction equation

HRID 2220202 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]=[CH:7][C:8]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:4]=2[CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]=[CH:7][C:8]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=3[N:10]([C:19](=[O:21])[CH3:20])[CH2:11][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69196263HCID 69196263, compound

Product 1

HCID 68892581HCID 68892581, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 8-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine (0.8 g, 2.5 mmole) in toluene (10 mL) was added acetic anhydride (1.2 mL, 12.5 mmole) and N,N-dimethylaminopyridine (1.51 g, 12.5 mmole). The reaction mixture was refluxed for 2 hours, concentrated and purified by flash chromatography over silica gel eluting with 30% ethyl acetate/hexane to give 1-(8-Bromo-2-chloro-6H-dibenzo[b,f]azocin-5-yl)-ethanone (0.65 g, 72%). 1HNMR (CDCl3) δ7.32 (d, 1H, J=1.76 Hz), 7.23 (dd, 1H, J=7.70, 1.76 Hz), 7.19 (m, 2H), 7.06 (d, 1H, J=8.80 Hz), 6.91 (d, 1H, J=8.36 Hz), 6.68 (d, 1H, J=13.16 Hz), 6.47 (d, 1H, J=12.76 Hz), 5.42 (d, 1H, J=14.96 Hz), 4.08 (d, 1H, J=15.36 Hz), 1.68 (s, 3H). HPLC Rt=4.05 min. m/z=362 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated
  3. custompurified by flash chromatography over silica gel eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f2ba1101139047dfa1e803a4ea50a76c
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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