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4-Bromotoluene → Benzene, 1-methyl-4-(phenylethynyl)-

HRID 12515
Notes
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Reaction equation

HRID 12515 reaction equation
[Li+].[C-:2]#[C:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O(B(OC(C)C)OC(C)C)[CH:11](C)C.Br[C:24]1[CH:29]=[CH:28][C:27](C)=[CH:26][CH:25]=1>COCCOC.COCCOC.C1COCC1.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:7]1([CH3:11])[CH:8]=[CH:9][C:4]([C:3]#[C:2][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 78054-BromotolueneHCID 21531Triisopropyl borateHCID 3437284Lithium phenylacetylide

Product 1

HCID 3014187Benzene, 1-methyl-4-(phenylethynyl)-

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8071
1,2-Dimethoxyethane
Solvent
HCID 22732251Tetrahydrofuran dimethoxyethaneSolvent

Conditions

Temperature
-78 °C

Procedure

General Procedure A. To a solution of lithium phenylacetylide (15.2 ml, 15.2 mmol) in DME (20 ml) under Argon at −78° C. was added triisopropoxylborane (3.5 ml, 15.2 mmol). The mixture was stirred at −78° C. for 1.5 hours. A solution of 1-bromo-4-methylbenzene (2 g, 11.7 mmol) in DME/THF (10 ml/10 ml) was degassed with dry argon, Pd(PPh3)4 (405 mg, 0.35 mmol) was added and the solution was degassed for another 5 min.

Workup

  1. additionwas added
  2. customthe solution was degassed for another 5 min.

Sources & evidence

ORD record
ord-ec8adad63d0041a0969484598bc2e2fd
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728014B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes