Acetic Acid → 1-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone

HRID 1949822Notes

Reaction equation

HRID 1949822 reaction equation
ClC1C=CC=CC=1CC(O)=O.[Br:12]C1C=CC2C3SC(C(OC)=O)=CC=3CCOC=2C=1.[Br:31][C:32]1[CH:33]=[CH:34][C:35]2[C:41]3[S:42][C:43]([C:45](=[O:54])[CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=4[Cl:53])=[CH:44][C:40]=3[CH2:39][CH2:38][O:37][C:36]=2[CH:55]=1.C(O)(=O)C>C(OCC)(=O)C.[Cu](Br)Br>[Br:31][C:32]1[CH:33]=[CH:34][C:35]2[C:41]3[S:42][C:43]([C:45](=[O:54])[CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=4[Cl:53])=[CH:44][C:40]=3[CH2:39][CH2:38][O:37][C:36]=2[CH:55]=1.[Br:12][CH:46]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[Cl:53])[C:45]([C:43]1[S:42][C:41]2[C:35]3[CH:34]=[CH:33][C:32]([Br:31])=[CH:55][C:36]=3[O:37][CH2:38][CH2:39][C:40]=2[CH:44]=1)=[O:54]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 17124o-Chlorophenylacetic acidHCID 56833843Methyl 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylateHCID 579002311-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone

Product 2

HCID 579002311-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanoneHCID 579003952-Bromo-1-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

1-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone (1.0 g, 2.3 mmol) was prepared by reaction of 2-chlorophenylacetic acid with methyl 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate. A solution of 1-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone in ethyl acetate (60 mL) was treated with copper(II) bromide (1.3 g, 5.8 mmol) in one portion in 100 mL rb flask. Acetic acid (2 mL) was added, and the flask sealed and heated at 85° C. After 8 hr, the reaction was removed from heat and allowed to stand overnight. The reaction mixture was concentrated to dryness, diluted with 100 mL diethyl ether and filtered through celite (ether wash). The eluent was re-filtered through the same celite pad, and concentration gave 2-bromo-1-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone as a crude solid used without purification.

Workup

  1. customthe flask sealed
  2. customthe reaction was removed
  3. temperaturefrom heat
  4. waitto stand overnight
  5. concentrationThe reaction mixture was concentrated to dryness
  6. additiondiluted with 100 mL diethyl ether
  7. filtrationfiltered through celite (ether wash)
  8. filtrationThe eluent was re-filtered through the same celite pad, and concentration

Sources & evidence

ORD record
ord-bc9b1df345264ce4852905d63db6cda6
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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