5-Bromo-2-chlorobenzaldehyde → HCID 66608092, compound

HRID 1514549Notes

Reaction equation

HRID 1514549 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:20])=[C:16]([CH:19]=1)[CH:17]=O>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:20])=[C:16]([CH2:17][C:8]2[S:7][C:6]3[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[CH:9]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 106089255-Bromo-2-chlorobenzaldehydeHCID 123986016-Chloro-1-benzothiophene

Product 1

HCID 66608092HCID 66608092, compound

Procedure

A solution of the above 6-chlorobenzo[b]thiophen-2-ylcarboxylic acid (3.0 g) and copper powder (1.2 g) in quinoline (20 ml) was stirred at 210° C. for 40 minutes. The mixture was cooled to room temperature and diluted with diethyl ether, and insoluble materials were filtered off. The filtrate was washed successively with 10% aqueous hydrochloric acid solution and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 6-chlorobenzo[b]thiophene (1.79 g) as colorless crystals. (3) The above 6-chlorobenzo[b]thiophene and 5-bromo-2-chlorobenzaldehyde obtained in Reference Example 16-(1) were treated in a manner similar to Reference Example 7 to give 5-bromo-2-chloro-1-(6-chlorobenzo[b]thiophen-2-ylmethyl)benzene as colorless crystals.

Workup

  1. additionwere treated in a manner similar to Reference Example 7

Sources & evidence

ORD record
ord-d5331a41910e41b4ab84e6a9a32323fd
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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