Ethyl 3-(bromophenyl)acetate → Ethyl 4-(3-bromophenyl)butanoate

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[CH3:2].[Br:16]C1C=C(CC(OCC)=O)C=CC=1>>[Br:16][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 11470552Ethyl 3-(bromophenyl)acetate2×

HCID 12870375Ethyl 4-(4-bromophenyl)butanoate2×

Product 1

HCID 11492759Ethyl 4-(3-bromophenyl)butanoate

Procedure

Employing the same general multistep preparation as for ethyl4-(4-bromophenyl)butanoate (Compound C), 60 g (246 mmol) of ethyl (3-bromophenyl)acetate (Compound B) was converted into the title compound (oil) using 255 ml (255 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M in hexane), 85.8 g (250 mmol) of (carbethoxymethylene)triphenylphosphorane and 1.7 g of 10% Pd/C.

Sources & evidence

ORD record: ord-fd88e66de55049f7ad9914c5bfbadd5a
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723666

Reaction notes

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