Sodium Carbonate → Methyl 3-bromobiphenyl-2-carboxylate

HRID 716006노트

반응식

HRID 716006 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 817273Methyl 2,6-dibromobenzoate

생성물 1

HCID 13352656Methyl 3-bromobiphenyl-2-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of the product from Example 114A (2.2 g, 7.5 mmol), phenylboronic acid (919 mg, 7.5 mmol), sodium carbonate (7.55 mL, 2 M aqueous solution, 15.1 mmol) tetrakis(triphenyphosphine)palladium(0) (261 mg, 0.23 mmol) and 50 mL of toluene were refluxed for 16 hours under nitrogen. The reaction was cooled and partitioned between 50 mL of water and 50 mL of ethyl acetate. The aqueous portion was separated and extracted with 2×25 mL of ethyl acetate and the combined organic extracts were washed with 2×25 mL of water and 1×25 mL of brine and dried over sodium sulfate. The organic solution was concentrated and the residue was purified via flash chromatography on a silica gel column (95:5 hexane:ethyl acetate) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.63 (s, 3H) 7.35-7.60 (m, 6H) 7.71-7.79 (m, 2H); MS (DCI+) m/z 308.0 [M+NH4]+.

후처리

  1. temperaturewere refluxed for 16 hours under nitrogen
  2. temperatureThe reaction was cooled
  3. custompartitioned between 50 mL of water and 50 mL of ethyl acetate
  4. customThe aqueous portion was separated
  5. extractionextracted with 2×25 mL of ethyl acetate
  6. washthe combined organic extracts were washed with 2×25 mL of water and 1×25 mL of brine
  7. dry with materialdried over sodium sulfate
  8. concentrationThe organic solution was concentrated
  9. customthe residue was purified via flash chromatography on a silica gel column (95:5 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-a7214b8699724064904a7ca49283ec19
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187483B2

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