Sodium Carbonate → 4-(4-Bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid

HRID 2373711노트

반응식

HRID 2373711 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([Br:12])[C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[C:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:15])=[O:14].C([O-])([O-])=O.[Na+].[Na+]>CC#N.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>[Br:12][C:5]1[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)[S:3][CH:4]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 86607173Methyl (2,4-dibromothien-3-yl)acetate

생성물 1

HCID 692003654-(4-Bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid수율 69.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

Pd(PPh3)4 (0.046 g, 0.4 mmol was added to a degassed solution of methyl (2,4-dibromothien-3-yl)acetate (2.51 g, 8 mmol) and 4-carboxybenzeneboronic acid (1.32 g, 8 mmol) in Na2CO3(40 mL, 0.4 M, 16 mmol) and CH3CN (40 mL). The mixture was heated to reflux overnight under argon for 16 h. The solution was filtered hot and the filtrate was concentrated to about half volume. The solution was extracted with CH2Cl2. The aqueous phase was acidified with concentrated HCl and the resulting solid was collected by vacuum filtration and washed with H2O to yield 4-(4-bromo-3-methoxycarbonylmethyl-thiophen-2-yl)-benzoic acid (1.98 g) which was used without further purification.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight under argon for 16 h
  3. filtrationThe solution was filtered hot
  4. concentrationthe filtrate was concentrated to about half volume
  5. extractionThe solution was extracted with CH2Cl2
  6. filtrationthe resulting solid was collected by vacuum filtration
  7. washwashed with H2O

출처 및 근거

ORD 기록
ord-cef14ed9fd214193955c414a410e118e
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459567B2

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