Toluene → Methanefluorodiphosphonate

HRID 1181910노트

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HRID 1181910 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 471181Methanefluorodiphosphonate수율 269.5%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

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온도
41 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cce75287da804760b74a693eba9eca36
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285658B2

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