Pyridine → 6-(2,4-Dichlorophenyl)-2-oxo-5-hexene-4-yl 2-Bromoacetate

HRID 354571Notes

Reaction equation

[Br:1][CH2:2][C:3](Br)=[O:4].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH:14]=[CH:15][CH:16]([OH:21])[CH2:17][C:18](=[O:20])[CH3:19].N1C=CC=CC=1>CCOCC>[Br:1][CH2:2][C:3]([O:21][CH:16]([CH:15]=[CH:14][C:8]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=1[Cl:6])[CH2:17][C:18](=[O:20])[CH3:19])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

2-Bromoacetyl bromide (1.1 ml, 13.2 mmole) was added dropwise to a stirred solution of 6-(2,4-dichlorophenyl)-4-hydroxy-5-hexene-2-one (3.4 g, 13.1 mmole) and pyridine (1.07 ml, 13.2 mmole) in ether (100 ml) at 0° C. The ice bath was removed and the reaction mixture was stirred at 20° C. for 2 hours and then diluted with H2O (100 ml). The organic layer was separated and washed with 1 N HCl (100 ml), H2O (2×100 ml) and brine, dried over MgSO4, filtered and evaporated. The residual oil was chromatographed on a 60 mm column with 15 cm of silica gel (230-400 mesh) Elution with methylene chloride-acetone (99:1; v:v; 1.9 L) provided the title compound (2.8 g, 56%); pmr (CDCl3) δ2.2 (3H, s), 2.92 (2H, t), 3.85 (2H, s), 5.9 (H, m), 6.15 (H, m) 6.95-7.5 (4H, m).

Workup

customThe ice bath was removed
additiondiluted with H2O (100 ml)
customThe organic layer was separated
washwashed with 1 N HCl (100 ml), H2O (2×100 ml) and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residual oil was chromatographed on a 60 mm column with 15 cm of silica gel (230-400 mesh) Elution with methylene chloride-acetone (99:1; v:v; 1.9 L)

Sources & evidence

ORD record: ord-1f0f5ef41632481589bc6cd4f7627bf8
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04375475

Reaction notes

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