3-Bromophenol → HCID 89585110, compound

HRID 1501137Notes

Reaction equation

HRID 1501137 reaction equation
[OH:1][C@@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[Br:14][C:15]1[CH:16]=[C:17](O)[CH:18]=[CH:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Br:14][C:15]1[CH:20]=[C:19]([CH:18]=[CH:17][CH:16]=1)[O:1][C@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 115633-BromophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 6932349HCID 6932349, compound

Product 1

HCID 89585110HCID 89585110, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 4-(1-hydroxyethyl)benzoate (1.8 g, 10 mmol), 3-bromophenol (1.9 g, 11 mmol) in 30 mL of anhydrous tetrahydrofuran was added Triphenyl phosphine (2.9 g, 11 mmol). The reaction mixture was stirred at room temperature for 0.5 hour under nitrogen atmosphere. Then diisopropylazodicarboxylate (2.4 g, 12 mmol) was added dropwise at 0° C., and the reaction mixture was stirred at room temperature for 12 hours. After the reaction, it was quenched with water, and the product was extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give (S)-methyl 4-(1-(3-bromophenoxy)ethyl)benzoate (2.2 g, 66%)

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction, it
  3. customwas quenched with water
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-48c648cf2f3b4644a46b59189d73e9a0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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