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

HRID 84559

반응식

HRID 84559 반응식
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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 2

HCID 24611Copper bromide (CuBr2)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b6e2e9cea0f849d092d4da1b9c104acb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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