Acetyl chloride → 7-Acetyl-5-(3-bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine

HRID 1983638Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH:4]=[C:5]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[CH2:6]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([C:19]1[C:7]2[CH2:6][C:5](=[CH:4][CH2:3][CH2:2][Br:1])[C:15]3[C:10]([O:9][C:8]=2[CH:16]=[CH:17][CH:18]=1)=[N:11][CH:12]=[CH:13][CH:14]=3)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of example 53, step 1 (7.2 g) in dichloromethane (70 ml) was added aluminum chloride (9.1 g) and acetyl chloride (3.2 ml), and the mixture stirred at 0° C. for 10 minutes. The reaction mixture was poured into ice. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The Residue was purified by silica gel chromatography, eluting with ethyl acetate-hexane (1:2) to give 7-acetyl-5-(3-bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine (7.9 g).

Workup

additionThe reaction mixture was poured into ice
extractionThe aqueous layer was extracted with ethyl acetate
washthe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried with magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe Residue was purified by silica gel chromatography
washeluting with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record: ord-8f2478ab05d94e28a15b136a5bd40758
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541365B2

Reaction notes

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