Bromotrimethylsilane → HCID 12968680, compound

HRID 854397Notes

Reaction equation

HRID 854397 reaction equation
C[O:2][P:3]([CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=[O:6])[O:4]C.Br[Si](C)(C)C>C(Cl)Cl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH2:7][P:3](=[O:2])([OH:6])[OH:4])(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 12968685HCID 12968685, compound

Product 1

HCID 12968680HCID 12968680, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diester 35 (0.58 g, 1.95 mmol) in dry CH2Cl2 (10 mL) and bromotrimethylsilane (1.5 mL, 11.7 mmol) was stirred at room temperature for 5 hours and then concentrated. The resulting residue was dissolved in anhydrous CH3OH (10 mL) and stirred at room temperature for 20 minutes. Insolubles were filtered, and the filtrate was concentrated. Purification by trituration with CH2Cl2 gave the phosphonic acid (iv) (0.51 g, 97%) as a white solid: 1H NMR (300 MHz, CD3OD) δH 3.17 (d, J=13.5 Hz, 2H), 7.35 (m, 2H), 7.97 (m, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in anhydrous CH3OH (10 mL)
  3. filtrationInsolubles were filtered
  4. concentrationthe filtrate was concentrated
  5. customPurification by trituration with CH2Cl2

Sources & evidence

ORD record
ord-96112f04bb8841218502a16e36bed203
Source dataset
uspto-grants-2007_08
Patent number
US07259172B2

Reaction notes

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