Hydrochloric Acid → HCID 70350198, compound

HRID 414055Notes

Reaction equation

HRID 414055 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH:11]1[O:16][C:15](=[O:17])[CH:14]=[CH:13][CH2:12]1.I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C@@H:11]1[O:16][C:15](=[O:17])[CH2:14][C@@H:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11575IodobenzeneHCID 13896199HCID 13896199, compound

Product 1

HCID 70350198HCID 70350198, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound (1a) (270 mg, 1.0 mmol), iodobenzene (224 mg, 1.1 mmol), triethylamine (160 μl, 1.1 mmol) and tetrakis(triphenylphosphine)palladium 10 mg) was placed under argon nd heated at 80° C. for 16 hours. The dark mixture was cooled and distributed between ethyl acetate (100 ml) and 1N HCl (100 ml). The organic layer was separated and washed with water (2×50 ml), dried and evaporated. The residue was purified by flash chromatography on silica gel using CHCl3 acetone, 20:1 (V:V) as eluant.

Workup

  1. temperatureThe dark mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9803bd48cf4f4b539b1c6a47808dbd98
Source dataset
uspto-grants-1988_12
Patent number
US04789682

Reaction notes

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