Sodium Carbonate → Biphenyl-3-ylacetic acid methyl ester

HRID 968334

反応式

HRID 968334 の反応式
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.CCCCCCC.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.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCCC>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1

参加物

10

反応物 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 66827Phenylboronic AcidHCID 11746402Methyl 2-(3-bromophenyl)acetate

生成物 1

HCID 10751722Biphenyl-3-ylacetic acid methyl ester

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 8900Heptane溶媒HCID 21899848Ethylacetate heptane溶媒

実験手順

Concentrated sulphuric acid (588 μL) was added to a solution of 3-bromophenyl acetic acid (10 g, 46.5 mmol) in methanol (100 mL). The mixture was refluxed for 1.5 h and then cooled to ambient temperature and evaporated under reduced pressure to afford a residue. The residue was redissolved in diethyl ether (500 mL), washed with water (2×100 mL), brine (100 mL), dried (MgSO4) and then evaporated under reduced pressure to afford 3-bromophenyl acetic acid methyl ester (10.65 g). The 3-bromophenyl acetic acid methyl ester was dissolved in toluene (117 mL) then phenyl boronic acid (6.8 g, 55.69 mmol) added, followed by a aqueous solution of sodium carbonate (93 mL, 2M) and tetrakis(triphenylphosphine)palladium (1.6 g, 1.41 mmol). The mixture was stirred overnight then cooled to ambient temperature and an aqueous solution of saturated ammonium chloride (100 mL) added. The mixture was extracted with ethyl acetate (2×200 mL), died (Na2SO4) and evaporated under reduced pressure to afford a residue. Flash chromatography of the residue over silica (200 g) using ethyl acetate:heptane (3:48) as the eluent gave biphenyl-3-yl acetic acid methyl ester, yield 10.5 g, (99%), TLC (single UV spot, Rf=0.24, 10% ethyl acetate in heptane), analytical HPLC Rt=19.55 min, HPLC-MS (single main UV peak with Rt=9.35 min, 227.1 [M+H]+).

後処理

  1. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  2. customevaporated under reduced pressure
  3. customto afford a residue

出典と根拠

ORDレコード
ord-bbc3b7027a51417b87a7c0c3175bf212
出典データセット
uspto-grants-2005_10
特許番号
US06958358B2

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