1,3-Dibromopropane → Ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate

HRID 40814Notes

Reaction equation

[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 4-(2-hydroxyphenoxy)butanoate (5.61 g, 25 mmol) in DMF (25 mL) at 0° C. was slowly added sodium hydride (0.6 g, 25 mmol) and then the solution was left stirring at 0° C. for 4 hours. To a stirred solution at 65-70° C. was added 1,3-dibromopropane (3.80 mL, 37.5 mmol). The resulting solution was continued to stir at 65-70° C. for 3 hours. Normal work-up and purification by silica gel column chromatography gave bromo-compound as a white solid in 60% yield (5.18 g, m.p. 31-32.6° C., CH2Cl2/hexane). 1H NMR (400 MHz, CDCl3): 1.25 (3H, t, J=7.1 Hz), 2.13 (2H, m), 2.34 (2H, m), 2.54 (2H, t, J=7.3 Hz), 3.64 (2H, t, J=6.4 Hz), 4.04 (2H, t, J=6.2 Hz), 4.10-4.15 (4H, m), 6.99-6.93 (4H, m).

Workup

customat 0° C.
waitthe solution was left
stirringto stir at 65-70° C. for 3 hours
customNormal work-up and purification by silica gel column chromatography
customgave bromo-compound as a white solid in 60% yield (5.18 g, m.p. 31-32.6° C., CH2Cl2/hexane)

Sources & evidence

ORD record: ord-99561d9a33f840289511af48f629bca8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530491B2

Reaction notes

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