Ethyl bromoacetate → HCID 22616837, compound

HRID 843213Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+].[Cl-].[Cl-].[Ca+2]>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

7.7 g (0.034 mol) of 4-(4-cyanophenylazo)phenol, 8.52 g (0.051 mol) ethyl bromoacetate (Fluka, pract.) and 5.66 g (0.041 mol) of dried K2CO3 were mixed in a 250 mL one-neck round flask fitted with a magnetic stirring bar. 100 mL of dry acetone was added, the flask was closed with a reflux condenser protected on the top with a CaCl2-drying tube and the stirred solution was refluxed on an oil bath at 60° C. for 72 h After cooling the flask was transferred to a Rotavapor and the acetone is removed by rotary evaporation. The resulting solid mixture was added 100 mL of 30° C. water and filtered. The filtercake was mixed with 50 mL of cold ethanol. After filtration and vacuum drying 9.19 g (yield 87%) of ethyl 2-[4-(4-cyanophenylazo)-phenoxy]-ethanoate was recovered.

Workup

customfitted with a magnetic stirring bar
customthe flask was closed with a reflux condenser
customdrying tube
temperatureAfter cooling the flask
customthe acetone is removed by rotary evaporation
additionThe resulting solid mixture was added 100 mL of 30° C. water
filtrationfiltered
additionThe filtercake was mixed with 50 mL of cold ethanol
filtrationAfter filtration and vacuum

Sources & evidence

ORD record: ord-0370eb4b1955485aa632cc6b391e3348
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376655B1

Reaction notes

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