Sodium Carbonate → HCID 59770332, compound

HRID 2218739Notes

Reaction equation

HRID 2218739 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([S:32][CH3:33])[CH:27]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:33][S:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 447547694,4,5,5-Tetramethyl-2-[3-(methylsulfanyl)phenyl]-1,3,2-dioxaborolane

Product 1

HCID 59770332HCID 59770332, compoundYield 79%

Procedure

Following procedures as described in Example 219, mix 5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (1 equivalent), 4,4,5,5-tetramethyl-2-(3-methylsulfanyl-phenyl)-[1,3,2]dioxaborolane (1.25 equivalents), 2N Na2CO3 (2 equivalents) and tetrakistriphenylphosphine palladium (0.05 equivalents)in a suitable solvent. Purify the product by silica gel chromatography to obtain a 79% yield of the title compound. MS(ES)=329(+)

Workup

  1. customPurify the product by silica gel chromatography

Sources & evidence

ORD record
ord-ccd07765284540a9a5f31ab03c14f059
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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