HCID 67983327, compound → HCID 86698217, compound

HRID 705398Notes

Reaction equation

HRID 705398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[P:9](OC)OC.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>C(OCC)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([P:9]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 67983327HCID 67983327, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 86698217HCID 86698217, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of dimethyl 2-methoxyphenylphosphonite (1.0 g, 5.0 mmol) in diethyl ether (40 mL) at 0° C. is added dropwise over 30 minutes a solution (1 M) of (4-chlorophenyl)magnesium bromide in diethyl ether (10.5 mL, 10.5 mmol). After allowing to warm to room temperature, the mixture is filtered and stripped to give an oil that is triturated with MeOH to give a white solid (0.98 g, 58%) 1H NMR (C6D6): δ 7.09 (m, 5H), 7.03 (m, 4H), 6.78 (m, 1H), 6.74 (m, 1H), 6.47 (d of d, 1H, J=8.2, 4.7), 3.16 (s, 3H); 13C NMR (C6D6): δ 161.47 (d, 1C, JCP=15.1 Hz), 135.88 (d, 2C, JCP=13.8 Hz), 135.52 (d, 4C, JCP=21.4), 135.30 (s, 2C), 133.74 (d, 1C, JCP=2.6 Hz), 130.86 (s, 1C), 128.99 (d, 4C, JCP=6.6 Hz), 125.60 (d, 1C, JCP=14.2 Hz), 121.47 (s, 1C), 110.64 (s, 1C), 55.15 (s, 1C); 31P NMR (C6D6) δ-16.54. Elemental analysis calculated for C19H15Cl2OP: C, 63.18; H, 4.19; 0, 4.43; P, 8.58. Measured: C, 63.31; H, 4.40.

Workup

  1. filtrationthe mixture is filtered
  2. customto give an oil that
  3. customis triturated with MeOH

Sources & evidence

ORD record
ord-b36bb6cff5a54640953a7f73db31bd8f
Source dataset
uspto-grants-2015_11
Patent number
US09174905B2

Reaction notes

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