Methanol → Dimethyl 4-bromoisophthalate

HRID 2246030

反応式

HRID 2246030 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]CCCCC.[CH3:25][OH:26]>>[CH3:25][O:26][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([C:11]([O:13][CH3:19])=[O:12])[CH:4]=1

参加物

5

反応物 4

HCID 887Methanol2 回HCID 1118Sulfuric AcidHCID 8058HexaneHCID 813614-Bromo-1,3-benzenedicarboxylic acid

生成物 1

HCID 2824912Dimethyl 4-bromoisophthalate収率 90%

実験手順

To a solution of 4-bromoisophthalic acid 201 (10 g, 40.8 mmol) in methanol (150 mL) was added concentrated sulfuric acid (3.5 mL). The solution mixture was heated at reflux temperature for 24 hours. After the reaction was complete, the methanol solvent was removed under reduced pressure. The residue was made basic with saturated sodium bicarbonate (NaHCO3). The solution was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate (Na2SO4). Removal of solvent gave oil, which solidified at ambient temperature. The solid was titurated twice with 20 mL of methanol and hexane (1:3) to give 8 g (90%) of 4-bromoisophthalic acid dimethyl ester 202: 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 3H), 3.93 (s, 3H), 7.74 (d, J=8 Hz, 1H), 7.95 (dd, J=2 Hz, J=8 Hz, 1H), 8.43 (d, J=2 Hz, 1H).

後処理

  1. temperatureThe solution mixture was heated
  2. temperatureat reflux temperature for 24 hours
  3. customthe methanol solvent was removed under reduced pressure
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulfate (Na2SO4)
  7. customRemoval of solvent
  8. customgave oil, which
  9. customsolidified at ambient temperature

出典と根拠

ORDレコード
ord-3d2641771cca4e64a65a6d6d60fe350e
出典データセット
uspto-grants-2010_03
特許番号
US07687236B2

関連ノート

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