反応 #48096

反応方程式

DMF

Oxalyl chloride

2-bromo-5-iodo-benzoic acid

→

crude product

4-Bromo-3-hydroxymethyl-1-iodo-benzene

溶媒

CH2Cl2

反応条件

後処理

1. 1
   濃縮Then, the solution is concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue is dissolved in THF (100 mL)
3. 3
   温度The resulting solution is cooled in an ice-bath
4. 4
   workup.ADDITIONLiBH4 (3.4 g) is added in portions
5. 5
   その他The cooling bath is removed
6. 6
   workup.STIRRINGthe mixture is stirred at room temperature for 1 h
7. 7
   workup.ADDITIONThe reaction mixture is diluted with THF
8. 8
   workup.ADDITIONtreated with 0.1 M hydrochloric acid
9. 9
   その他Then, the organic layer is separated
10. 10
    抽出the aqueous layer is extracted with ethyl acetate
11. 11
    乾燥The combined organic layers are dried (Na2SO4)
12. 12
    その他the solvent is evaporated under reduced pressure

実験手順

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid in CH2Cl2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiBH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product.

出典