1-Bromo-2-iodobenzene → 4-Bromotolan-4'-carboxylic acid-tert.-butyl ester

HRID 974220Notes

Reaction equation

HRID 974220 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(NCC)C.C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:20]2[CH:21]=[CH:22][C:17]([Br:16])=[CH:18][CH:19]=2)=[CH:11][CH:12]=1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 114151-Bromo-2-iodobenzeneHCID 11776TriphenylphosphineHCID 13965008Tert-butyl 4-ethynylbenzoate

Product 1

HCID 679318664-Bromotolan-4'-carboxylic acid-tert.-butyl ester

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8021DiethylamineSolvent

Conditions

Temperature
40 °C

Procedure

2.8 g (Ph3P)2PdCl2 and 400 mg of CuI are added to a solution of 40.4 g of 4-ethinyl-benzoic acid tert.-butyl ester, 56.6 g of bromoiodobenzene and 1.34 g of Ph3P in 50 ml of diethylamine and 300 ml of absolute acetonitrile and the reaction mixture is stirred for 72 hours at 40° C., suction filtered and dried.

Workup

  1. filtrationsuction filtered
  2. customdried

Sources & evidence

ORD record
ord-888987550c094b79965c4cfa1e2713d9
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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