Hydrochloric Acid → HCID 18434394, compound

HRID 2306081Notes

Reaction equation

HRID 2306081 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>O.CS(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 18434394HCID 18434394, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent3×

Procedure

A solution of 50% (w/w) NaOH in water (188 mL) in DMSO (800 mL) was stirred at room temperature until a precipitate formed, treated dropwise with a solution of 4-bromophenol (101.2 g) in DMSO (200 mL) over 25 minutes, stirred for 25 minutes, treated with ethyl 4-chloro-3-oxobutanoate (102.2 g) over 40 minutes, adjusted to pH 3 with 6M HCl, treated with water (200 mL) over 12 minutes, stirred for 5 hours, treated with water (150 mL) over 20 minutes, and filtered. The solid was washed with sequentially with water and 40% ethanol/water and dried under vacuum (100 mm Hg) at 50° C. with a nitrogen bleed to provide 119.8 g of the desired product. 1H NMR (300 MHz, CDCl3) δ7.40 (m, 2H), 6.79 (m, 2H), 4.65 (s, 2H), 4.20 (q, 2H, J=7 Hz), 3.62 (s, 2H), 1.26 (t, 3H, J=7Hz).

Workup

  1. customformed
  2. stirringstirred for 5 hours
  3. filtrationfiltered
  4. washThe solid was washed with sequentially with water and 40% ethanol/water
  5. customdried under vacuum (100 mm Hg) at 50° C. with a nitrogen

Sources & evidence

ORD record
ord-caced4baff374a27a04768cabdd5160c
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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