Hydrochloric Acid → Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

HRID 1803355

反応式

HRID 1803355 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1F.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[Br:16]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 79178Dimethyl 2-fluoroterephthalate

生成物 1

HCID 57839250Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-fluoro-terephthalic acid dimethyl ester 2j (10 g, 47.1 mmol), 2-bromophenol 1j (6.0 mL, 51.8 mmol) and potassium carbonate (7.16 g, 51.8 mmol) in N,N-dimethylformamide (100 mL) was heated at 100° C. for 36 h. The mixture was allowed to cool to rt, then poured into cold dilute hydrochloric acid (0.5 N, 350 mL). The product was extracted into EtOAc, washed with water (4×) and brine (1×) and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel using dichloromethane as the eluant. The crude product was isolated (10.5 g) and used without further purification in the subsequent reaction. MS: m/z 365 (MH+).

後処理

  1. temperatureto cool to rt
  2. extractionThe product was extracted into EtOAc
  3. washwashed with water (4×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-3b6bbe30d0784a069bed7f4477c767f3
出典データセット
uspto-grants-2013_01
特許番号
US08350041B2

関連ノート

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