Boron tribromide → HCID 178476790, compound

HRID 1960115Notes

Reaction equation

HRID 1960115 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH2:13][PH:14](=[O:18])[O:15][CH2:16][CH3:17])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][PH:14](=[O:18])[O:15][CH2:16][CH3:17])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178476791HCID 178476791, compound

Product 1

HCID 178476790HCID 178476790, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (3.16 mL, 1 M solution in DCM) was added to a solution of ethyl (3-methoxyphenyl)methylphosphinate (0.169 g, 0.789 mmol) in DCM at 0° C. The reaction was stirred at rt for 15 h, then partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.35-7.40 (m, 1H), 7.19-7.26 (m, 2H), 7.05 (dd, 1H, J=8.3, 2.6 Hz), 3.85-4.05 (m, 2H), 1.69 (d, 3H, J=14.6 Hz), 1.29 (t, 3H, J=7.1 Hz).

Workup

  1. custompartitioned between EtOAc and saturated aqueous NaHCO3
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0dff076d24e44e1ba374a4665b03b2f9
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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