Tributylphosphine → 4-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acid methyl ester

HRID 1914328Notes

Reaction equation

HRID 1914328 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[Br:48][C:49]1[CH:54]=[CH:53][C:52](O)=[CH:51][C:50]=1[CH:56]1[O:61][CH2:60][CH2:59][CH2:58][O:57]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:15][C:52]2[CH:53]=[CH:54][C:49]([Br:48])=[C:50]([CH:56]3[O:57][CH2:58][CH2:59][CH2:60][O:61]3)[CH:51]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 215731464-Bromo-3-[1,3]dioxan-2-yl-phenolHCID 59518172Methyl 4-(1-hydroxy-3-methylbutyl)benzoate

Product 1

HCID 671533784-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(1-hydroxy-3-methyl-butyl)-benzoic acid methyl ester (1600 mg, 7.21 mmol) in toluene (72 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 2728 mg, 10.81 mmol) at 0° C., followed by the additions of tributylphosphine (2.69 mL, 10.81 mmol) and 4-bromo-3-[1,3]dioxan-2-yl-phenol (2240 mg, 8.65 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 (1000 mg).

Workup

  1. washeluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving the titled compound (1000 mg)

Sources & evidence

ORD record
ord-e0eca23b09634d4b9a0613f71791fa12
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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