3-Bromoaniline → 3-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

HRID 1913855Notes

Reaction equation

HRID 1913855 reaction equation
[OH:1][C:2]([CH3:9])([CH3:8])[C:3]#[C:4]C(O)=O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C:63]1[CH:64]=[C:65]([CH:67]=[CH:68][CH:69]=1)[NH2:66]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:66][C:65]1[CH:64]=[C:63]([C:4]#[C:3][C:2]([CH3:9])([OH:1])[CH3:8])[CH:69]=[CH:68][CH:67]=1

Participants

7

Reactant 4

HCID 115623-BromoanilineHCID 2724141Tetrabutylammonium FluorideHCID 31641664-Hydroxy-4-methylpent-2-ynoic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 1122363-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 3-liter 4-neck flask provided with a mechanical stirrer there are introduced—in the order—64.0 g (0.50 mol, 1.0 eq.) of 4-hydroxy-4-methyl-2-pentinoic acid, 5.7 g of Pd(OAc)2 (5% mol), 24 g of XPhos (2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; 10% mol) and 378 g (1.5 mol, 3 eq. mol.) of TBAF (Tetra-n-butylammonium fluoride). The mixture is dissolved, under Argon atmosphere, in 2 L of distilled anhydrous THF. 55 ml of 3-Bromoaniline (d=1.585 g/mL, 0.5 mol, 1.0 eq. mol.) are added to this solution.

Workup

  1. customIn a 3-liter 4-neck flask provided with a mechanical stirrer there

Sources & evidence

ORD record
ord-9fa1cbfe82414cc1a96a190905433b5d
Source dataset
uspto-grants-2013_12
Patent number
US08609841B2

Reaction notes

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