Hydrochloric Acid → Dimethyl 5-(4-fluorophenoxy)isophthalate

HRID 1889644

反応式

HRID 1889644 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(N(CC)CC)C.FOB(C1C=CC=CC=1)O.Cl>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO.CCOC(C)=O.C(Cl)(Cl)Cl>[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:1][C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:19][CH:18]=1

参加物

11

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 2856454-Fluorophenylboronic acidHCID 66616553HCID 66616553、化合物2 回

生成物 1

HCID 66616627Dimethyl 5-(4-fluorophenoxy)isophthalate収率 85%

試薬・触媒・溶媒 5

HCID 8895Cupric acetate触媒2 回HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of dimethyl 5-hydroxyisophthalate (3.1 g, 14.75 mmol), 4-fluorophenylboronic acid (4.13 g, 29.5 mmol), copper(II) acetate (2.68 g, 14.75 mmol) and triethylamine (4.48 g, 44.2 mmol) in CH2Cl2 (65 mL) was stirred at rt in the open air for 38 h. An additional 1 g of fluorophenylboronic acid was added and the reaction mixture was continued to stir at rt in the open air. After 24 h, an additional 1 g of fluorophenylboronic acid and 300 mg of copper acetate were added to the reaction mixture and it was continued to stir for 6 h in the open air. The mixture was mixed with CHCl3 and aq HCl, the organic layer was separated, washed with aq HCl, aq NaHCO3, dried over MgSO4, concentrated, and the residue was purified by flash column chromatography on SiO2 eluting with Hexane:EtOAc:MeOH/800:200:40 to obtain the desired product (3.8 g, 12.49 mmol, 85% yield) as a white solid. 1H NMR (CDCl3): δ 8.36 (s, 1H), 7.75 (s, 2H), 7.06˜6.96 (m, 4H), 3.89 (s, 6H).

後処理

  1. stirringto stir at rt in the open air
  2. waitAfter 24 h
  3. stirringto stir for 6 h in the open air
  4. customthe organic layer was separated
  5. washwashed with aq HCl, aq NaHCO3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customthe residue was purified by flash column chromatography on SiO2 eluting with Hexane

出典と根拠

ORDレコード
ord-245c996330624509804f3899d4307b31
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

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