Phosphoric Acid → HCID 10950439, compound

HRID 991977Notes

Reaction equation

HRID 991977 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5]O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OP(O)(O)=O.[I-:42].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5][I:42]

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 5238Sodium IodideHCID 14812Phosphorus oxide (P4O10)HCID 11131640HCID 11131640, compound

Product 1

HCID 10950439HCID 10950439, compoundYield 79%

Conditions

Temperature
120 °C

Procedure

3,5-Dichloro-4-(4-methoxy-3-isopropylphenoxy)-benzylalcohol (3.21 g) (Example 6a) was added into a mixture of P2O5 (576 mg) and H3PO4 (5.5 ml) followed by addition of sodium iodide (2.43 g). The mixture was stirred at 120° C. for 15 min and then partitioned between water and ethyl acetate. The organic layer was washed with an aqueous solution of Na2S2O3 and brine, dried, filtered and concentrated. The residue was crystallized from petroleum ether to give 2.9 g (79%) of 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)benzyliodide.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of Na2S2O3 and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-59b67d79256c47359ba44cedfa3f7f53
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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