Dimethylformamide → HCID 20071127, compound

HRID 981830Notes

Reaction equation

HRID 981830 reaction equation
[Si]([O:8][C:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C:38]1[CH:43]=[CH:42][CH2:41][C:40](OC)([Cl:44])[CH:39]=1.CN(C)[CH:49]=[O:50]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.C(OC)(C)(C)C.O>[Cl:44][C:40]1[CH:41]=[CH:42][C:43]([CH:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][CH2:18][C:9]2=[O:8])=[CH:38][C:39]=1[O:50][CH3:49]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 2724141Tetrabutylammonium FluorideHCID 15777972HCID 15777972, compoundHCID 20071128HCID 20071128, compound

Product 1

HCID 20071127HCID 20071127, compound

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
90 °C

Procedure

Charge an oven dried, argon flushed 25-mL 2-necked round bottomed flask equipped with a stirring bar and reflux condenser with 2-t-butyldimethylsilyloxy-3,4-dihydronaphthalene (0.5007 grams, 1.9224 mmoles) and tetra-n-butylammonium fluoride (2.3 mL, 2.30 mmoles, 1 M in tetrahydrofuran), stir for a few minutes and then add 4-bromo-2-methoxy-2-chlorobenzene (0.4287 grams, 1.9356 mmoles), dichlorobis(tri-o-tolyl-phosphine)palladium (0.0154 grams, 0.0196 mmoles) and 5 mL dimethylformamide. Heat the reaction mixture for 18 hours (oil bath temperature about 90° C.), cool to RT and add 5 mL water and 10 mL t-butylmethyl ether. Separate the layers, extract the aqueous layers with 3×5 mL t-butylmethyl ether, wash the combined organic layers with water and saturated salt solution, dry over magnesium sulfate and concentrate using a Buchi rotavapor to yield the product.

Workup

  1. additionCharge an oven
  2. customdried
  3. customargon flushed 25-mL 2-necked round bottomed flask
  4. customequipped with a stirring bar
  5. temperaturecool to RT
  6. customSeparate the layers
  7. extractionextract the aqueous layers with 3×5 mL t-butylmethyl ether
  8. washwash the combined organic layers with water and saturated salt solution
  9. dry with materialdry over magnesium sulfate
  10. concentrationconcentrate
  11. customto yield the product

Sources & evidence

ORD record
ord-834d4ebb04ca44a5b7c04bdac1683853
Source dataset
uspto-grants-1991_02
Patent number
US04992591

Reaction notes

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