Cesium carbonate → HCID 68957549, compound

HRID 2108664Notes

Reaction equation

HRID 2108664 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:28])[CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]COC)=[C:11]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:10]=1.CC1C=CC(S(O[CH2:40][P:41]([CH3:46])(=[O:45])[O:42][CH2:43][CH3:44])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:27][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH:10]=1)[O:28][CH2:40][P:41]([CH3:46])(=[O:45])[O:42][CH2:43][CH3:44]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58196244HCID 58196244, compound2×HCID 68532630HCID 68532630, compound

Product 1

HCID 68957549HCID 68957549, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,5-dichloro-4-[3′-(4-fluorobenzyl)-4′-methoxymethoxybenzyl]phenol (0.08 gm, 0.19 mmol), acetonitrile (3 mL), ethyl [(4-methylphenyl)sulfonyloxymethyl]methylphosphinate (compound 74, 0.105 gm, 0.38 mmol), was added cesium carbonate (0.153 gm, 0.47 mmol). The reaction was heated at reflux for 2 hours, then stirred over night at r.t. The reaction was filter into 25 ml ethyl acetate, washed 1× with brine, dried over Na2SO4, filtered and concentrated. Ethyl [(3,5-dichloro-4-(3-(4-fluorobenzyl)-4-hydroxybenzyl)phenoxy)methyl]methylphosphinate was obtained by prep plate TLC using a 2 mm×20×20 cm SiO2 plate eluted with ethyl acetate. (0.06 gm, 60%); 1H NMR (300 MHz, DMSO-d6): δ 7.23 (s, 2H), 7.17 (m, 2H), 7.07 (t, J=8.7 Hz, 2H), 6.95 (m, 2H), 6.86 (m, 1H), 5.14 (s, 2H), 4.41 (m, 2H), 4.07 (s, 2H), 4.04 (m, 2H), 3.86 (s, 2H), 3.25 (s, 3H); 31p NMR (121.4 MHz, DMSO-d6): δ 46.13; TLC conditions: Uniplate silica gel, 250 microns; ethyl acetate; Rf=0.22.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction was filter into 25 ml ethyl acetate
  4. washwashed 1× with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2192877e6c654868b1a84d171cbbcbcf
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

Loading…