Triacetoxyperiodinane → 4-Fluoro-3-nitrobenzaldehyde

HRID 58144

反応式

HRID 58144 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 41675874-Fluoro-3-nitrobenzyl alcohol

生成物 1

HCID 5981294-Fluoro-3-nitrobenzaldehyde収率 76.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (4-fluoro-3-nitro-phenyl)-methanol (750 g, 4.4 mmol) in DCM (40 mL) at 0° C. was added Dess-Martin Reagent (3.0 g, 7 mmol). The solution was stirred at room temperature for 4 hours. TLC showed disappearance of starting material. The reaction was quenched with 10% NaHCO3 and 10% Na2S2O3 aqueous solution and DCM layer separated and washed with water (100 mL) and brine (50 mL). The reaction was concentrated, and the residue was purified by flash chromatography on silica to obtain the title compound (570 mg, yield: 75%). 1H-NMR (400 MHz, DMSO-d6) δ 10.09 (d, 1H), 8.36 (t, 1H), 8.06 (dd, 1H), 7.97 (m, 1H).

後処理

  1. customThe reaction was quenched with 10% NaHCO3 and 10% Na2S2O3 aqueous solution and DCM layer
  2. customseparated
  3. washwashed with water (100 mL) and brine (50 mL)
  4. concentrationThe reaction was concentrated
  5. customthe residue was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-035f7c5189544f81a4b89988e3a1348d
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

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