Benzyl Chloride → 7-Benzyloxy-benzo[b]thiophene-4-carbaldehyde

HRID 394226Notes

Reaction equation

HRID 394226 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC2C=CC=[C:26]([OH:27])C1=2.C(Cl)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].COC(Cl)Cl>CN(C)C=O.ClCCl>[CH2:1]([O:8][C:9]1[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[C:12]([CH:26]=[O:27])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21004Methane, dichloromethoxy-HCID 110840501-Benzothiophen-7-olHCID 226475147-Benzyloxy-benzo[b]thiophene

Product 1

HCID 226476117-Benzyloxy-benzo[b]thiophene-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 2 a], 7-benzyloxy-benzo[b]thiophene (prepared from benzo[b]thiophen-7-ol [J. Chem. Soc., Perkin Trans. 1 (1983), (12), 2973-71 and benzylchloride by treatment with potassium carbonate in N,N-dimethylformamide at room temperature) was reacted with dichloromethyl methyl ether in dichloromethane at 0° C. to give 7-benzyloxy-benzo[b]thiophene-4-carbaldehyde.

Sources & evidence

ORD record
ord-1277264d31a1479f9586d07221516730
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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