Sodium Carbonate → (4'-Fluorobiphenyl-2-yl)methanol

HRID 76856

反応式

HRID 76856 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.O.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][OH:15])=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 728502-Bromobenzyl alcoholHCID 2856454-Fluorophenylboronic acid

生成物 1

HCID 1392777(4'-Fluorobiphenyl-2-yl)methanol

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
115 °C

実験手順

To a mixture of 4-fluorophenylboronic acid (2.5 g, 13.4 mmol), 2-bromobenzyl alcohol (2.81 g, 20.1 mmol) and Pd(PPh3)4 (0.25 g, 0.216 mmol) in DME (20 mL) is added an aqueous solution of Na2CO3 (11.5 mL, 2.7 M, 31 mmol). The mixture is heated to 115° C. in sealed vessel overnight. The reaction is allowed to cool to room temperature and is diluted with EtOAc and water. The aqueous layer is extracted further with EtOAc (2×). The combined organic layers are washed with water, saturated NH4Cl, brine and dried over Na2SO4. After concentration, the resulting residue is purified by flash chromatography (hexane/CH2Cl2) to give (4′-fluorobiphenyl-2-yl)-methanol as oil. (cas #773871-75-3) 1H NMR (400 MHz, CDCl3) δ (ppm) 7.46-7.43 (m, 1H), 7.32-7.22 (m, 4H), 7.18-7.16 (m, 1H), 7.04-6.99 (m, 2H), 4.48 (d, J=5.5 Hz, 2H), 1.68 (br s, 1H).

後処理

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer is extracted further with EtOAc (2×)
  3. washThe combined organic layers are washed with water, saturated NH4Cl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe resulting residue is purified by flash chromatography (hexane/CH2Cl2)

出典と根拠

ORDレコード
ord-35d1dfceb3c64f939831b842566e1a97
出典データセット
uspto-grants-2014_09
特許番号
US08835646B2

関連ノート

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