Hydrogen Bromide → 2-Bromo-4-chlorobenzoic acid

HRID 6968

반응식

HRID 6968 반응식
[N+]([O-])([O-])=O.[Na+].N[C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[BrH:17]>O.[Cu](Br)Br>[Br:17][C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

참가 물질

6

반응물 3

HCID 260Hydrogen BromideHCID 24268Sodium NitrateHCID 666462-Amino-4-chlorobenzoic acid

생성물 1

HCID 331262-Bromo-4-chlorobenzoic acid수율 59%

시약·촉매·용매 2

HCID 24611Copper bromide (CuBr2)촉매HCID 962Water용매3회

실험 절차

An aqueous solution of sodium nitrate (2.21 g) in water (15 mL) is added dropwise to a stirred, ice-cooled mixture of 2-amino-4-chlorobenzoic acid (5.00 g, 29.1 mmol) and 48% hydrobromic acid (150 mL) in water (150 mL). The resultant mixture is stirred for 2 hr at 0° C. Then it is treated dropwise with an aqueous solution of copper bromide (7.81 g) in water (20 mL). Upon the completion of the addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred overnight. After extraction with ethyl acetate/hexanes (3:1; 2×400 mL), the combined organic layers are washed with brine (200 mL), dried, concentrated, and chromatographed on silica (1% methyl alcohol and 0.5% acetic acid in chloroform) to give the title compound (4.04 g, 59% yield). mp 154–155° C.; ES(−)MS m/z 233, (M−H)− consistent with 1 Br an 1 Cl.

후처리

  1. temperaturecooled
  2. additionUpon the completion of the addition
  3. extractionAfter extraction with ethyl acetate/hexanes (3:1; 2×400 mL)
  4. washthe combined organic layers are washed with brine (200 mL)
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed on silica (1% methyl alcohol and 0.5% acetic acid in chloroform)

출처 및 근거

ORD 기록
ord-09dbf5b4d43440c18a10b96ec12ac8d1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

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