Acetonitrile → 1,3-Benzodioxole-5-carboxylic acid, 2,2-difluoro-, methyl ester

HRID 17899

反応式

HRID 17899 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[CH:3]=1.C(#N)C.C(N(CC)CC)C>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:5][O:6][C:7]([C:2]1[CH:12]=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[CH:3]=1)=[O:8]

参加物

6

反応物 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 27362715-Bromo-2,2-difluoro-1,3-benzodioxole

生成物 1

HCID 591292611,3-Benzodioxole-5-carboxylic acid, 2,2-difluoro-, methyl ester収率 212.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

A solution of 5-bromo-2,2-difluoro-benzo[1,3]dioxole (11.8 g, 50.0 mmol) and tetrakis(triphenylphosphine)palladium (0) [Pd(PPh3)4, 5.78 g, 5.00 mmol] in methanol (20 mL) containing acetonitrile (30 mL) and triethylamine (10 mL) was stirred under a carbon monoxide atmosphere (55 PSI) at 75° C. (oil bath temperature) for 15 hours. The cooled reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by silica gel column chromatography to give crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g), which was used directly in the next step.

後処理

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-edfbf038504c4393a41073ca08ade4db
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

関連ノート

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