Sodium Carbonate → Methyl 3-bromobiphenyl-2-carboxylate

HRID 716006ノート

反応式

HRID 716006 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 13352656Methyl 3-bromobiphenyl-2-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-a7214b8699724064904a7ca49283ec19
出典データセット
uspto-grants-2015_11
特許番号
US09187483B2

反応ノート

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