Sodium Hydroxide → HCID 68718410, compound

HRID 1173321Notes

Reaction equation

HRID 1173321 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[C:14]([CH3:17])([CH3:16])[CH3:15].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[OH-].[Na+]>COCCOC.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:14]([C:3]1[CH:4]=[C:5]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 742994-Chlorophenylboronic acidHCID 14963255HCID 14963255, compound

Product 1

HCID 68718410HCID 68718410, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 9.0 g (30.1 mmol) of 2-bromo-1,5-di-tert-butyl-3-methoxybenzene (Zhang, H.; Kwong, F. Y.; Tian, Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886-6890) in 100 mL of DME was purged with nitrogen for 15 min and 1.5 g (0.13 mmol) of tetrakis(triphenylphosphine)palladium(0) was added. After stirring 20 min 5.0 g (31.9 mmol) of 4-chlorobenzeneboronic acid was added. The reaction mixture was stirred at 75° C. and 15 mL of 5 N sodium hydroxide was added dropwise. The resulting mixture was then stirred overnight at 80° C. The reaction mixture was then cooled to room temperature and the DME was removed in vacuo. The residue was partitioned between water and hexane containing 10% EtOAc and extracted. The organic layer was dried, filtered and evaporated to afford the title compound suitable for use in the next step.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was then stirred overnight at 80° C
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customthe DME was removed in vacuo
  5. customThe residue was partitioned between water and hexane containing 10% EtOAc
  6. extractionextracted
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6e0d219790cf434f82b79a2e5663510c
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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