乙腈 → 2,2-二氟胡椒酸甲酯

HRID 17899

反应方程式

HRID 17899 反应方程式
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]

参与物

6

反应物 3

HCID 6342乙腈HCID 8471三乙胺HCID 27362715-溴-2,2-二氟-1,3-苯并二恶茂

产物 1

HCID 591292612,2-二氟胡椒酸甲酯收率 212.8%

试剂、催化剂与溶剂 2

HCID 178418397HCID 178418397，化合物催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
75 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-edfbf038504c4393a41073ca08ade4db
来源数据集
uspto-grants-2010_06
专利号
US07741321B2

关联笔记

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