Phenetole → HCID 71110860, compound

HRID 576358Notes

Reaction equation

HRID 576358 reaction equation
[Br:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5]([Cl:11])=[C:4]([C:12]([OH:14])=O)[CH:3]=1.C(Cl)(C(Cl)=O)=O.BrC1C2SC=CC=2C(Cl)=C(C(Cl)=O)C=1.[CH2:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5]([Cl:11])=[C:4]([C:12]([C:41]2[CH:42]=[CH:43][C:38]([O:37][CH2:35][CH3:36])=[CH:39][CH:40]=2)=[O:14])[CH:3]=1

Participants

8

Reactant 5

HCID 7674PhenetoleHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 71076950HCID 71076950, compoundHCID 86714064HCID 86714064, compound

Product 1

HCID 71110860HCID 71110860, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

After dissolving crude 7-bromo-4-chlorobenzo[b]thiophene-5-carboxylic acid 97 (847 mg, 2.91 mmol) in CH2Cl2, (COCl)2 (0.49 mL, 5.82 mmol) and catalytic amount DMF was added carefully at 0° C. The resulting solution was stirred overnight at room temperature. The volatiles were evaporated under reduced pressure and dried in vacuo. The crude compound was used for the next step without further purification. To a solution of crude 7-bromo-4-chlorobenzo[b]thiophene-5-carbonyl chloride in CH2Cl2 (50 mL) was added ethoxybenzene (462 mg, 3.78 mmol) and AlCl3 (464 mg, 3.49 mmol) at 0° C. After warming the reaction mixture up to room temperature, it was stirred for 4 hours. The resulting compound was quenched with aq. NH4Cl solution and the normal work-up with EtOAc was conducted. Purification by silica gel chromatography gave the title compound (917 mg, 79.8%) as an off-white solid.

Workup

  1. additionwas added carefully at 0° C
  2. customThe volatiles were evaporated under reduced pressure
  3. customdried in vacuo
  4. customThe crude compound was used for the next step without further purification
  5. temperatureAfter warming the reaction mixture up to room temperature, it
  6. stirringwas stirred for 4 hours
  7. customThe resulting compound was quenched with aq. NH4Cl solution
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7b3d7bf142924e24bc38788de504e5d7
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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