Hydrochloric Acid → HCID 57975908、化合物

HRID 2388954ノート

反応式

HRID 2388954 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:14][Mg]Br.C(OCC)(=O)C.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([OH:13])[CH3:14])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 108003705-Bromo-3-formyl-2-hydroxybenzoic acidHCID 178418573HCID 178418573、化合物

生成物 1

HCID 57975908HCID 57975908、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.0 g (4.1 mmol) of 5-bromo-3-formyl-2-hydroxy-benzoic acid was dissolved in 100 mL of anhydrous THF under nitrogen. The solution was cooled in an ice-bath and 13.6 ml of a 3 M solution of methyl magnesium bromide was added. The mixture was stirred for 16 h, slowly warming to room temperature. The resulting solution was distributed between ethyl acetate and dilute aqueous hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and evaporated to afford 1.09 g of 5-bromo-2-hydroxy-3-(1-hydroxy-ethyl)-benzoic acid as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 7.76 (d, 1H), 7.72 (d, 1H), 4.98 (q, 1H), 1.30 (d, 3H), MS: m/z 258.9+261.0 (M+H+).

後処理

  1. temperatureThe solution was cooled in an ice-bath
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-9799cc5f15df4e7798a954b7515dad9a
出典データセット
uspto-grants-2012_09
特許番号
US08268994B2

反応ノート

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