Dimethylformamide → HCID 58626146, compound

HRID 1161662Notes

Reaction equation

HRID 1161662 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(CC)CC)C.[C:18]1([C:24]#[C:25][CH2:26]O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C)C=[O:31]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:26]#[C:25][CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:31])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1231153-Phenyl-2-propyn-1-olHCID 111847502-CHLORO-4-IODO-1-METHOXYBENZENE

Product 1

HCID 58626146HCID 58626146, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring mixture of 3-chloro-4-methoxyiodobenzene (0.3 g, 1.1 mmol), (PPh3)2PdCl2 (31 mg, 0.044 mmol), triethylamine (1.2 mL, 8.9 mmol) in dimethylformamide (3 mL) was added to phenylethynylcarbinol (0.29 g, 2.2 mmol) at temperature in the range of 20-40° C. under nitrogen atmosphere. The mixture was then stirred at 80° C. for 12 hours. After cooling the mixture to temperature in the range of 20-40° C. it was diluted with water (15 mL) and extracted with ethyl acetate (3×25 mL). The organic layers were collected, combined, washed with water (2×5 mL), dried over anhydrous sodium sulphate, and concentrated to give the desired compound.

Workup

  1. temperatureAfter cooling the mixture to temperature in the range of 20-40° C. it
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. customThe organic layers were collected
  4. washwashed with water (2×5 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f549c2365d94058acb21879e603863d
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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