Cesium carbonate → 3-(4-Bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl ester

HRID 2354994ノート

反応式

HRID 2354994 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][O:17][C:18](=[O:30])[C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([O:26][CH2:27][O:28][CH3:29])[CH:20]=1>N1C=CC=CC=1.[Cu]=O>[CH3:16][O:17][C:18](=[O:30])[C:19]1[CH:20]=[C:21]([O:26][CH2:27][O:28][CH3:29])[CH:22]=[C:23]([O:25][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:9])[CH:4]=2)[CH:24]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 23136427Methyl 3-hydroxy-5-(methoxymethoxy)benzoate

生成物 1

HCID 687084713-(4-Bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl ester収率 65%

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 1049Pyridine溶媒

反応条件

温度
130 °C

実験手順

After adding 20.4 g (0.68 mol) of 1-bromo-2-fluoro-4-iodobenzene, 20.8 g (0.64 mol) of cesium carbonate and 5.07 g (0.64 mol) of copper (II) oxide to a solution of 9.00 g (0.43 mol) of 5-hydroxy-3-methoxymethoxybenzoic acid methyl ester in pyridine (50.0 ml), the mixture was stirred at 130° C. for 8 hours under a nitrogen atmosphere. The reaction mixture was filtered and then concentrated under reduced pressure, acetic acid ethyl ester and saturated aqueous ammonium chloride were added to the obtained residue, and the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=9:1) to obtain 10.6 g of 3-(4-bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl ester (yield: 65%) as a yellow oil.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure, acetic acid ethyl ester and saturated aqueous ammonium chloride
  3. additionwere added to the obtained residue
  4. washthe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=9:1)

出典と根拠

ORDレコード
ord-76e136b49dca4799bb8314ebf0d1548c
出典データセット
uspto-grants-2010_07
特許番号
US07754743B2

反応ノート

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