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

HRID 17899

반응식

HRID 17899 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-edfbf038504c4393a41073ca08ade4db
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741321B2

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