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Hydrochloric Acid → (2-(4-Bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester

HRID 2229534
Notes
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Reaction equation

HRID 2229534 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8](=[O:19])[C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[OH:18])=[C:4]([F:22])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].Cl>CC(C)=O>[C:34]([O:33][C:31](=[O:32])[CH2:30][O:18][C:10]1[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=1[C:8](=[O:19])[NH:7][CH2:6][C:5]1[CH:20]=[CH:21][C:2]([Br:1])=[CH:3][C:4]=1[F:22])([CH3:37])([CH3:36])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 18468202N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-5-nitro-benzamide

Product 1

HCID 22093497(2-(4-Bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-5-nitro-benzamide (0.95 g, 2.6 mmol) in acetone (15 mL, 0.2 M) was treated with aq K2CO3 (2 M, 1.9 mL, 3.8 mmol) and t-butyl bromoacetate (2.2 mL, 8.4 mmol). After heating to 50° C. for 30 h, the reaction was acidified to pH 1-2 with 2 N HCl and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated aq NaCl, dried over Na2SO4, filter ed and concentrated. The crude oil was crystallized from heptane and ethyl acetate to give [2-(4-bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester as a white crystalline solid (1.21 g, 97%): 1H NMR (DMSO-d6, 300 MHz) δ 9.01 (br t, J=5.7 Hz, 1H), 8.58 (d, J=3.0 Hz, 1H), 8.33 ( dd, J1=9.0 Hz, J2=3.0 Hz, 1H), 7.51 (br d, J=9.6 Hz, 1H), 7.42-7.34 (m, 2H), 7.32 (d, J=9.3 Hz, 1H), 4.99 (s, 2H), 4.52 (d, J=5.7 Hz, 2H), 1.40 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrated
  6. customThe crude oil was crystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-4ca0d67d34aa4dd3bb36492cf14348e1
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06420426B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes