Tributylphosphine → 4-[1-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl]-benzoic acid methyl ester

HRID 1160926Notes

Reaction equation

HRID 1160926 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[Br:47][C:48]1[C:53]([CH3:54])=[CH:52][C:51](O)=[CH:50][C:49]=1[CH3:56]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:14][C:51]2[CH:52]=[C:53]([CH3:54])[C:48]([Br:47])=[C:49]([CH3:56])[CH:50]=2)[CH:11]([CH3:12])[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 819704-Bromo-3,5-dimethylphenolHCID 595181984-(1-Hydroxy-2-methyl-propyl)-benzoic acid methyl ester

Product 1

HCID 671534754-[1-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(1-hydroxy-2-methyl-propyl)-benzoic acid methyl ester (5000 mg, 24.04 mmol) in toluene (240 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 9098 mg, 36.06 mmol) at 0° C., followed by the additions of tributylphosphine (8.98 mL, 36.06 mmol) and 4-bromo-3,5-dimethyl-phenol (5798 mg, 28.85 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving the titled compound (5540 mg).

Workup

  1. washeluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving the titled compound (5540 mg)

Sources & evidence

ORD record
ord-eac97956a27a4926a8579fcf69698825
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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