Butyl bromide → 6'-Butoxy-2,6-dichloro-4',5'-dimethoxy-2'-methylbenzophenone

HRID 582381Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[C:8]([O:15][CH3:16])[C:7]=1[OH:17])=[O:5].[K].Br[CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C=O>[CH2:25]([O:17][C:7]1[C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[CH:10]=[C:11]([CH3:12])[C:6]=1[C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:22])[CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,6-dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methyl-benzophenone, potassium salt (1.13 g; 3 mmol), 1-bromobutane (0.69 g, 5 mmol) and dimethyl formamide (5 ml) are stirred at 100° C. for 8 h, and concentrated in vacuo. The residue is dissolved by shaking with a toluene/water mixture, after separation, the organic layer is collected washed with water and dried. After addition of silica gel (5 g), the solvent is evaporated. A flash chromatography column is packed with silica gel (25 g) and the charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (95/5, 500 ml) gives the title compound, 0.82 g, (69% y) as colourless crystals, mp. 70° C.

Workup

concentrationconcentrated in vacuo
dissolutionThe residue is dissolved
stirringby shaking with a toluene/water mixture
customafter separation
customthe organic layer is collected
washwashed with water
customdried
additionAfter addition of silica gel (5 g)
customthe solvent is evaporated
washElution with petrol ether/ethyl acetate (95/5, 500 ml)

Sources & evidence

ORD record: ord-cb63e542319b49e4839f0202d2ac75e8
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922919

Reaction notes

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