1,1-Dibromoethane → 1-Bromo-2-(4-benzyloxy-2-nitrophenoxy)ethane

HRID 440128Notes

Reaction equation

C([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)C1C=CC=CC=1.[C:18]([O-:21])([O-])=O.[K+].[K+].[Br:24][CH:25](Br)[CH3:26]>CN(C=O)C.CCOCC>[Br:24][CH2:25][CH2:26][O:14][C:11]1[CH:12]=[CH:13][C:8]([O:21][CH2:18][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-benzyl-2-nitrophenol (1.3 g, 5.3 mmol) and K2CO3 (1.2 g, 8.7 mmol) in DMF (10 mL) was stirred for 10 min. Dibromoethane (1.4 mL, 16.2 mmol) was added to the reaction mixture and heated at 70° C. for 24 hrs. The reaction mixture was diluted with ether (30 mL) and washed with water (20 mL) and brine (20 mL). The ether layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was fractionated by flash chromatography (4:1 hexane/ethyl acetate) yielding bromoethane 6 as a yellow oil (1.3 g, 88%). 1H NMR: 3.65 (t, J=5 Hz, 2H), 4.35 (t, J=5 Hz, 2H), 5.05 (s, 2H), 7.0-7.5 (m, 8H).

Workup

washwashed with water (20 mL) and brine (20 mL)
dry with materialThe ether layer was dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d7573c1ee44e49548009e79c59c6e572
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05516911

Reaction notes

Loading…