Ethyl bromoacetate → HCID 67032460, compound

HRID 920581Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:9][CH:8]=1.CCN(CC)CC.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CC#N>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][N:15]1[CH2:16][CH2:17][O:18][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]3[C:3]([Cl:2])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:23])=[CH:12][CH:11]=2)[CH2:14]1)[CH3:37]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine hydrochloride (0.65 g; 1.68 mmol), Et3N (0.58 mL; 4.2 mmol), and ethyl bromoacetate (0.24 ml; 2.19 mmol) in CH3CN (65 mL) was stirred at 85° C., overnight. After cooling to RT the mixture was concentrated in vacuo and the residue partitioned between water and CH2Cl2. The layers were separated and aqueous layer was extracted once more with CH2Cl2. The combined organic layers were concentrated in vacuo and the residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1) to afford {2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-acetic acid ethyl ester (0.62 g).

Workup

temperatureAfter cooling to RT the mixture
concentrationwas concentrated in vacuo
customthe residue partitioned between water and CH2Cl2
customThe layers were separated
extractionaqueous layer was extracted once more with CH2Cl2
concentrationThe combined organic layers were concentrated in vacuo
customthe residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1)

Sources & evidence

ORD record: ord-09abfe6a42324688ad7b7825f340c53e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273017B2

Reaction notes

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