Triethylamine → HCID 21939609, compound

HRID 1242802Notes

Reaction equation

HRID 1242802 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.O1CCOCC1.[CH3:18][C:19]1([CH3:26])[C:23]([CH3:25])([CH3:24])[O:22][BH:21][O:20]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:18][C:19]1([CH3:26])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=2)[O:20]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 312751,4-DioxaneHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane2×

Product 1

HCID 21939609HCID 21939609, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-4-isopropoxybenzene was combined with dioxane (10.5 mL) and dichloropalladium(dppf) dichloromethane complex (36 mg) under argon. 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (0.96 mL) was added followed by triethylamine (1.29 mL). The reaction was heated to 90° C. for 23 hours after which, dichloropalladium(dppf) dichloromethane complex (36 mg), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.96 mL) and triethylamine (1.29 mL) was added. Heating was continued for an additional 19 hours after which, it was cooled to room temperature and diluted with ethyl acetate (25 mL). The mixture was washed with water (2×20 mL) and brine (20 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the residue on silica gel (0% to 50% ethyl acetate/hexane over 40 minutes) gave 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isopropoxybenzene (544 mg). Yield=47%.

Workup

  1. additionwas added
  2. temperatureHeating
  3. washThe mixture was washed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue on silica gel (0% to 50% ethyl acetate/hexane over 40 minutes)

Sources & evidence

ORD record
ord-f78268def02a409db2fafb5679b810c8
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

Loading…