4-(3-Bromophenoxy)butanoic acid → 8-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

HRID 627833ノート

反応式

HRID 627833 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:9](=[O:11])[CH2:8][CH2:7][CH2:6][O:5][C:4]=2[CH:3]=1

参加物

3

反応物 1

HCID 23844144-(3-Bromophenoxy)butanoic acid

生成物 1

HCID 103770258-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one収率 50.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
110 °C

実験手順

To a stirred suspension of polyphosphoric acid (PPA, ca. 60 g) and celite (ca. 40 g) in 100 mL toluene was added crude 4-(3-bromophenoxy)butanoic acid 7 (ca. 58 mmol) in one portion, 10 mL toluene rinse. The resultant suspension was heated at 110° C. for 5 hr. The toluene was decanted through a plug of celite and the remaining slurry was washed repeatedly with toluene and ethylacetate. The eluent was concentrated and purified by flash column chromatography (4:1 hex:EtOAc) to give 8-bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one (7 g, ca. 50% y) 8. 1H NMR (DMSO-d6, 500 MHz) 7.55 (d, J=8.5 Hz, 1H), 7.37 (d, J=1.5 Hz, 1H), 7.35 (dd, J=8.5, 1.5 Hz, 1H), 4.24 (t, J=6.5 Hz, 2H), 2.79 (t, J=7.0 Hz, 2H), 2.14 (m, 2H).

後処理

  1. washrinse
  2. customThe toluene was decanted through a plug of celite
  3. washthe remaining slurry was washed repeatedly with toluene and ethylacetate
  4. concentrationThe eluent was concentrated
  5. custompurified by flash column chromatography (4:1 hex:EtOAc)

出典と根拠

ORDレコード
ord-b105700aff7a46a69eb26d227827724a
出典データセット
uspto-grants-2016_04
特許番号
US09309265B2

反応ノート

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