Sodium Carbonate → 6-(4-Chlorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde

HRID 624373ノート

反応式

HRID 624373 の反応式
Br[C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.CCOCC.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>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([CH:11]=[O:12])=[CH:4][C:5]3[O:9][CH2:8][O:7][C:6]=3[CH:10]=2)=[CH:16][CH:15]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 950621,3-Benzodioxole-5-carboxaldehyde, 6-bromo-

生成物 1

HCID 866428736-(4-Chlorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 6-bromobenzo[d][1,3]dioxole-5-carbaldehyde (4.6 g), 4-chlorophenylboronic acid (3.78 g) and tetrakis(triphenylphosphine)palladium(0) (0.232 g) in toluene (80 mL) and methanol (30 mL) was added 2N aqueous Na2CO3 (30 mL). The mixture was stirred at reflux overnight. The mixture was diluted with ether (400 mL) and washed with water, brine and dried over Na2SO4. After filtration and concentration of the solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give the product.

後処理

  1. temperatureat reflux overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration of the solvent
  5. washeluted with 3% ethyl acetate in hexane
  6. customto give the product

出典と根拠

ORDレコード
ord-7249493d16b04d209be8c49e3d2a5f49
出典データセット
uspto-grants-2016_04
特許番号
US09303025B2

反応ノート

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