Dimethylformamide → 4-Chloro-2,3-dihydro-benzo[b]oxepine-5-carbaldehyde

HRID 628033Notes

Reaction equation

HRID 628033 reaction equation
P(Cl)(Cl)([Cl:3])=O.[O:6]1[CH2:12][CH2:11][C:10](=O)[CH2:9][C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]1=2.CN([CH:21]=[O:22])C>>[Cl:3][C:10]1[CH2:11][CH2:12][O:6][C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[C:9]=1[CH:21]=[O:22]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 125800312,3,4,5-Tetrahydro-1-benzoxepin-4-one

Product 1

HCID 579003964-Chloro-2,3-dihydro-benzo[b]oxepine-5-carbaldehyde

Procedure

Phosphorus oxychloride (1.4 ml, 15.2 mmol) was added dropwise to anhydrous DMF (5 ml) at 0° C. After 30 minutes a solution of 2,3-dihydro-5H-benzo[b]oxepin-4-one (980 mg, 6.04 mmol) in anhydrous DMF (5 ml) was added dropwise and this was allowed to stir at room temperature for 2 days. The reaction mixture was then added to ice water, and the ice allowed to melt before extracting into ethyl acetate and washing with water and brine to give 4-chloro-2,3-dihydro-benzo[b]oxepine-5-carbaldehyde.

Workup

  1. extractionbefore extracting into ethyl acetate
  2. washwashing with water and brine

Sources & evidence

ORD record
ord-36e59434b5d141108497944c2cd06087
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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