Acetic Acid → Methyl 3-bromo-2,6-dihydroxybenzoate

HRID 488664

反応式

HRID 488664 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11].C(O)(=O)C.[Br:17]Br>ClCCl>[Br:17][C:8]1[C:9]([OH:10])=[C:4]([C:5]([OH:11])=[CH:6][CH:7]=1)[C:3]([O:2][CH3:1])=[O:12]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 24408BromineHCID 519869Methyl 2,6-dihydroxybenzoate

生成物 1

HCID 22271916Methyl 3-bromo-2,6-dihydroxybenzoate収率 58.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of methyl-2,6-dihydroxybenzoate (1.68 g, 10.0 mmol) in dichloromethane (10 mL) was added acetic acid (1 mL), followed by drop-wise addition of bromine (515 μL, 10.0 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at ambient temperature for 1 hour, concentrated under reduced pressure, co-evaporated with ethyl acetate (2×). The resulting solid was triturated with hexane/ethyl acetate and re-crystallized from hot hexane/ethyl acetate to provide the titled compound (1.45 g). MS ESI(−,) m/e 244, 246 (M−H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.45 (s, 1H), 10.19 (s, 1H), 7.46 (d, 1H), 6.41 (d, 1H), 3.84 (s, 3H).

後処理

  1. concentrationconcentrated under reduced pressure, co-evaporated with ethyl acetate (2×)
  2. customThe resulting solid was triturated with hexane/ethyl acetate
  3. customre-crystallized from hot hexane/ethyl acetate

出典と根拠

ORDレコード
ord-7ac0adb4e27146a2b885afeb3cb107a7
出典データセット
uspto-grants-2005_12
特許番号
US06972340B2

関連ノート

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