Acetyl chloride → 7-bromo-3,4-dihydro-1H-2-benzopyran-1,3-dione

HRID 2170123ノート

反応式

HRID 2170123 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][C:12]([OH:14])=[O:13])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C>>[Br:1][C:2]1[CH:10]=[C:6]2[C:5]([CH2:11][C:12](=[O:13])[O:14][C:7]2=[O:9])=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 6367Acetyl chlorideHCID 106349875-Bromo-2-(carboxymethyl)benzoic acid

生成物 1

HCID 185077967-bromo-3,4-dihydro-1H-2-benzopyran-1,3-dione

実験手順

A oven-dried 10 mL round-bottomed flask containing a stirring bar was charged with 5-bromo-2-(carboxymethyl)benzoic acid (500 mg, 1.93 mmol). Freshly distilled acetyl chloride (5.0 ml) was added, the flask was fitted with a condenser and the reaction mixture was refluxed under an argon atmosphere for 16 h. The reaction was then cooled to room temperature and the excess acetyl chloride was removed in vacuo. The solid obtained was triturated with Et2O (5.0 mL), filtered and dried to give 7-bromoisochroman-1,3-dione as an off white solid (404.7 mg, 87%). Spectral data for this compound were consistent with those in the literature. M.p. 176-178° C. (lit.7 M.p. 171-173° C.); 1H NMR (400 MHz, DMSO-d6): δ=8.13 (s, 1H), 7.94 (d, J=8.2 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 4.23 (s, 2H).

後処理

  1. additionA oven-dried 10 mL round-bottomed flask containing a stirring bar
  2. customthe flask was fitted with a condenser
  3. temperaturethe reaction mixture was refluxed under an argon atmosphere for 16 h
  4. customthe excess acetyl chloride was removed in vacuo
  5. customThe solid obtained
  6. customwas triturated with Et2O (5.0 mL)
  7. filtrationfiltered
  8. customdried

出典と根拠

ORDレコード
ord-f9786715f91449ed90040e33e3a71298
出典データセット
uspto-grants-2015_06
特許番号
US09050586B2

反応ノート

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