Bromine → Bromine

HRID 226270노트

반응식

HRID 226270 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1.[Br:15][Br:16]>C(O)(=O)C>[Br:15][C:12]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:13]#[N:14])=[CH:9][CH:8]=[CH:7]2.[Br:15][Br:16]

참가 물질

5

반응물 2

HCID 24408BromineHCID 113443927-Methoxynaphthalene-1-carbonitrile

생성물 2

HCID 24408BromineHCID 688504788-Bromo-7-methoxy-1-naphthonitrile

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Bromination of 7-methoxy-1-naphthonitrile (4) with bromine in acetic acid is a very temperature sensitive reaction. The compound 8-bromo-7-methoxy-1-naphthonitrile is produced rapidly at room temperature with two equivalent of bromine. It produces many poly-brominated impurities when the temperature is above 70° C. In this process of the present invention, 7-methoxy-1-naphthonitrile (4) is di-brominated at 40-70° C. with 2-6 equivalents of bromine in acetic acid. Upon the completion of the reaction, the reaction mixture is quenched with excess sodium bisulfite to reduce excess bromine and the product precipitates and is isolated with an expected yield on the order of 90-95% with high purity. This dibromide, without further purification, is heated with stannous chloride in a mixture of acetic acid and concentrated HCl at 100° C. The bromine in 8 position is selectively reduced. The product, 3-bromo-7-methoxy-1-naphthonitrile (6) is filtered from the reaction mixture after the reaction is complete. Typically, the yield is 70-80% over 2 steps with 95%+HPLC purity.

후처리

  1. customa very temperature sensitive reaction

출처 및 근거

ORD 기록
ord-b16d63e05e9f4bda8723ee3ff4e1a1b5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557237B2

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