Butyl vinyl ether → 1-Benzo[b]thiophen-4-yl-2-bromo-ethanone

HRID 33567Notes

Reaction equation

HRID 33567 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=[CH:9][C:2]1=2.[Br:13]C1C2C=CSC=2C=CC=1.C(OCCCC)=C>[Pd]>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10](=[O:12])[CH2:11][Br:13])=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 8108Butyl vinyl etherHCID 120942084-Bromobenzo[b]thiopheneHCID 224741261-(Benzo[b]thiophen-4-yl)ethanone

Product 1

HCID 574553111-Benzo[b]thiophen-4-yl-2-bromo-ethanone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-benzo[b]thiophen-4-yl-2-bromo-ethanone was synthesised from 1-benzo[b]thiophen-4-yl-ethanone (available by the palladium coupling of 4-bromobenzo[b]thiophene with 1-vinyloxy-butane) according to the method in Example 10A(a) (6.8 g, 92%) as an orange oil; 1H NMR (CDCl3): 4.6 (2H, s), 7.4 (1H, t, J=7.8 Hz), 7.65 (1H, d, J=5.7 Hz), 7.95 (1H, dd, J=7.8, 0.9 Hz), 8.1 (1H, dt, J=7.8, 0.9 Hz), 8.3 (1H, dd, J=5.7, 0.9 Hz).

Sources & evidence

ORD record
ord-c15c5fe751c94059b248fab455fb969d
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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