Sodium Carbonate → HCID 66756816, compound

HRID 1642637Notes

Reaction equation

HRID 1642637 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15]Br)[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[C:22]=1[C:23]#[N:24].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.C(Cl)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>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[CH2:15][C:25]1[CH:26]=[CH:27][CH:28]=[C:21]([CH3:20])[C:22]=1[C:23]#[N:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzeneHCID 667570262-methyl-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 66756816HCID 66756816, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (2.99 g, 9.27 mmol) and Pd(PPh3)4 (536 mg, 0.464 mmol) in DME (10 mL) is heated to 60° C. for 2 min. in a microwave. 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (5.96 g of crude, ˜13.9 mmol) in DME (10 mL) and EtOH (2 mL) is added along with Na2CO3 (2 M, 3.3 mL). The reaction mixture is heated to 110° C. for 30 min. by microwave. Then the reaction is heated to 120° C. for an additional 15 min. by microwave. The reaction mixture is diluted with DCM (150 mL) and extracted with water (50 mL). The aqueous layer is extracted with DCM (30 mL) and the combined organics is dried over Na2SO4. Evaporation yields a brown oil, and it is then purified by flash column to yield a tan solid as the title compound: MS (M−H)−=357.2.

Workup

  1. temperatureThe reaction mixture is heated to 110° C. for 30 min. by microwave
  2. temperatureThen the reaction is heated to 120° C. for an additional 15 min. by microwave
  3. extractionextracted with water (50 mL)
  4. extractionThe aqueous layer is extracted with DCM (30 mL)
  5. dry with materialthe combined organics is dried over Na2SO4
  6. customEvaporation
  7. customyields a brown oil, and it
  8. customis then purified by flash column

Sources & evidence

ORD record
ord-a533f2e851034182b7e3ffad2cf13a18
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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