Toluene → Methanefluorodiphosphonate

HRID 1817513ノート

反応式

HRID 1817513 の反応式
[F:1][CH:2]([P:13](=[O:22])([O:18]C(C)C)[O:14]C(C)C)[P:3](=[O:12])([O:8]C(C)C)[O:4]C(C)C.C[Si](Br)(C)C.C1(C)C=CC=CC=1.C(N(CCCC)CCCC)CCC>ClCCCl.CN(C=O)C>[F:1][CH:2]([P:13](=[O:14])([OH:22])[OH:18])[P:3](=[O:4])([OH:12])[OH:8]

参加物

7

反応物 4

HCID 1140TolueneHCID 7622TributylamineHCID 76113BromotrimethylsilaneHCID 12722940Tetrapropan-2-yl (fluoromethylene)bis(phosphonate)

生成物 1

HCID 471181Methanefluorodiphosphonate収率 269.5%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
41 °C

実験手順

To a stirred solution of tetraisopropyl fluoromethylenediphosphonate (320 mg, 0.88 mmol) in 1,2-dichloroethane (5 mL) was added dropwise trimethylsilyl bromide (0.70 mL, 5.28 mmol). The resulting solution was stirred at 40-42° C. for 24 h and 3 mL of anhydrous toluene was added. The mixture was concentrated to dryness, and coevaporated with toluene once. The residue was redissolved in DMF (3 mL)/water (2 mL) mixture and concentrated. The residue was mixed with DMF (2 mL) and tributylamine (0.42 mL, 1.76 mmol) and then concentrated to dryness. The residue was coevaporated with anhydrous DMF two times. The resulting residue was dried in a vacuum oven at 30° C. overnight to give a slightly yellow residue (460 mg).

後処理

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionThe residue was redissolved in DMF (3 mL)/water (2 mL) mixture
  3. concentrationconcentrated
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was dried in a vacuum oven at 30° C. overnight

出典と根拠

ORDレコード
ord-001da96a64ec4180911e9d50ff0a49b6
出典データセット
uspto-grants-2009_10
特許番号
US07598230B2

反応ノート

読み込み中…