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

HRID 53308

Reaction equation

HRID 53308 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[Br:16]C1C=C(CC(OCC)=O)C=CC=1>>[Br:16][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:2]=1

Participants

3

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 ethyl 4-(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-baf3153e0aee4c7b907510d1c5905477
Source dataset
uspto-grants-1997_04
Patent number
US05618943

Linked notes

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