Thionyl Chloride → Methyl 2-(4-(bromomethyl)phenyl)acetate

HRID 339938

反応式

HRID 339938 の反応式
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[C:17]([O-])(O)=O.[Na+]>CO.C1(C)C=CC=CC=1.O>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:17])=[O:11])=[CH:7][CH:8]=1

参加物

7

反応物 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 45190564-(Bromomethyl)phenylacetic acid

生成物 1

HCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of p-bromomethylphenylacetic acid (50.0 g, 218 mmol) in MeOH (125 g) and toluene (250 g), was added thionyl chloride (15.6 g) dropwise at 0° C. and stirred for 3 hr. Separately NaHCO3 (33 g, 393 mmol) was dissolved in water (540 g), mixed with toluene (200 g) and cooled to 0° C. The reaction solution described above was added dropwise to the mixture and stirred for 1 hr. The aqueous layer was removed and the organic layer washed with water. The solution was then concentrated under reduced pressure at a temperature below 40° C. to give the subtitle compound as a crude product (58.9 g) used directly in the following reaction. 1H NMR (DMSO-d6) δ 7.37 (d, 2H), 7.34 (d, 2H), 4.62 (s, 2H), 3.73 (s, 2H), 3.63 (s, 3H)

後処理

  1. additionabove was added dropwise to the mixture
  2. stirringstirred for 1 hr
  3. customThe aqueous layer was removed
  4. washthe organic layer washed with water
  5. concentrationThe solution was then concentrated under reduced pressure at a temperature below 40° C.

出典と根拠

ORDレコード
ord-6c511b199ecd4ff0a0654ecc319f86ea
出典データセット
uspto-grants-2014_11
特許番号
US08895570B2

関連ノート

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