4-Bromophenol → HCID 58005733, compound

HRID 623931Notes

Reaction equation

HRID 623931 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.O[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 84152Methyl 3-hydroxypivalateHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 58005733HCID 58005733, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

40% Diethyl azodicarboxylate-toluene solution (9.54 mL) was added to a tetrahydrofuran (40 mL) solution containing 4-bromophenol (2.0 g), methyl hydroxypivalate (2.77 g) and triphenylphosphine (5.49 g), and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10) to obtain methyl 3-(4-bromophenoxy)-2,2-dimethylpropanoate (3.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=90:10)

Sources & evidence

ORD record
ord-0062fff14129444fbbc19abafe9793db
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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