Triethylsilane → Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]-2-methylpropionate

HRID 2121842Notes

Reaction equation

[Br:1][CH2:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:6]=1[Cl:20])=O.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][CH2:2][CH2:3][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]([CH3:16])([CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:6]=1[Cl:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-[4-(2-bromoacetyl)-3-chlorophenoxy]-2-methylpropionate (209 mg) in trifluoroacetic acid (445 μl) was added triethylsilane (300 μl), and the mixture was stirred for 1 hour at 60° C. After the reaction mixture was concentrated under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent:hexane/ethyl acetate=30/1) gave ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]-2-methylpropionate (171 mg).

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent:hexane/ethyl acetate=30/1)

Sources & evidence

ORD record: ord-05ca38b579e445b2897a8dbe6e7637de
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696489B1

Reaction notes

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