Hydrochloric Acid → HCID 57669519, compound

HRID 2174352Notes

Reaction equation

HRID 2174352 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])([O-])=O.[K+].[K+].Cl>O.CC#N>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 57669519HCID 57669519, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-bromophenyl)phenol (3.74 g, 15.0 mmol), MeCN (20 ml), ethyl 4-bromobutyrate (4.42 g, 22.7 mmol), and K2CO3 (3.12 g, 22.6 mmol) was stirred at 80° C. After 16 h water (100 ml) and 1N HCl (40 ml) were added, and the product was extracted (3×AcOEt), the combined extracts were washed with brine (2×), dried (MgSO4), and concentrated. The residue was recrystallized from EtOH (40 ml) to yield 4.35 g (80%) of 4-(4′-bromobiphenyl-4-yloxy)butyric acid ethyl ester as colorless plates.

Workup

  1. extractionthe product was extracted (3×AcOEt)
  2. washthe combined extracts were washed with brine (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from EtOH (40 ml)

Sources & evidence

ORD record
ord-015dac2dac4e44a2bb6252c0923217ec
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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