4-Bromophenol → 1-Benzofuran-5-carbaldehyde

HRID 978311Notes

Reaction equation

HRID 978311 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.BrC1C=C[C:15]([OH:18])=CC=1.C(OC(OCC)CBr)C>>[O:6]1[CH:7]=[CH:8][C:4]2[CH:3]=[C:2]([CH:15]=[O:18])[CH:10]=[CH:9][C:5]1=2

Participants

4

Reactant 3

HCID 78084-BromophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 90015Benzofuran, 5-bromo-

Product 1

HCID 27738751-Benzofuran-5-carbaldehyde

Procedure

benzo[b]furan-5-carboxaldehyde was prepared from 5-bromobenzo[b]furan (prepared from 4-bromophenol and bromoacetaldehyde diethyl acetal by the general method described in J. Chem. Soc. Perkin 1, 1972, 556) following essentially the same procedure as that described in (b) above. Benzo[b]furan-5-carboxaldehyde was obtained as an oil. Pmr spectrum (CDCl3 ; δ in ppm): 6.90 (1H, d); 7.55-7.93 (3H, m); 8.15 (1H, d); 10.08 (1H, s).

Sources & evidence

ORD record
ord-6afed5888439414b933ffeb56dbfa1b0
Source dataset
uspto-grants-1987_05
Patent number
US04664693

Reaction notes

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