Hypophosphoric acid → Methyl 3-bromo-5-methoxybenzoate

HRID 495979

반응식

HRID 495979 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1N)[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].P(P(O)(O)=O)(O)(O)=O>C(O)C.S(=O)(=O)(O)O.C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

8

반응물 3

HCID 24536Hypophosphoric acidHCID 22324265Methyl 4-amino-3-bromo-5-methoxybenzoateHCID 23668193Sodium Nitrite

생성물 1

HCID 15618226Methyl 3-bromo-5-methoxybenzoate수율 100.2%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

A 500 ml round bottom flask fitted with overhead stirring was charged with 16.5 grams (55 mmole) of methyl 3-bromo-5-methoxy-4-aminobenzoate in 80 ml ethanol, 15 ml sulfuric acid and 20 ml acetic acid. The solution was chilled in an ice bath and 6.6 gms (95 mmole) of sodium nitrite in 30 ml water was added dropwise while maintaining the temperature below 10° C. After stirring an additional 25 minutes, 100 ml of 50% hypophosphoric acid was added and the mixture was stirred cold for 2 hours. The reaction mixture was diluted with 500 ml water, extracted with ether, and then evaporated under reduced pressure to give 13.5 grams of methyl 3-bromo-5-methoxybenzoate as a reddish oil.

후처리

  1. customA 500 ml round bottom flask fitted with overhead
  2. temperatureThe solution was chilled in an ice bath
  3. temperaturewhile maintaining the temperature below 10° C
  4. stirringAfter stirring an additional 25 minutes
  5. stirringthe mixture was stirred cold for 2 hours
  6. extractionextracted with ether
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-fa90fa7b37da4b90a2a2326e63d108da
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943169B2

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