Dimethylformamide → (Z)-8-bromo-5-chloro-2,3-dihydrobenzo[b]oxepine-4-carbaldehyde

HRID 84405Notes

Reaction equation

HRID 84405 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:16](=O)[CH2:15][CH2:14][CH2:13][O:12][C:11]=2[CH:18]=1.CN([CH:22]=[O:23])C>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2=[C:11]([CH:18]=1)[O:12][CH2:13][CH2:14][C:15]([CH:22]=[O:23])=[C:16]2[Cl:3]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychloride2×HCID 103770258-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 57900258(Z)-8-bromo-5-chloro-2,3-dihydrobenzo[b]oxepine-4-carbaldehyde

Procedure

Phosphorus oxychloride, POCl3 (1.88 mL, 20.8 mmol) was added dropwise to DMF (5 mL) at 0° C. After 30 min a solution of 8-bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one 8 (2.0 g, 8.3 mmol) in 8 mL DMF was added dropwise. The reaction mixture was allowed to reach room temperature to stir 2 hr, then poured slowly over rapidly stirred ice water. The aqueous phase was extracted with ethylacetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated to give 9.

Workup

  1. customto reach room temperature
  2. extractionThe aqueous phase was extracted with ethylacetate
  3. washthe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give 9

Sources & evidence

ORD record
ord-d75cfacc22aa499d9872260b5601991a
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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