tert-Butanol → 1463053-89-5

HRID 2203204Notes

Reaction equation

HRID 2203204 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.CC[N:14]([CH2:17]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])=CC=1.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>C1(C)C=CC=CC=1>[C:36]([O:40][C:17](=[O:26])[NH:14][C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:2]=1[Br:1])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 331232-bromo-3-chlorobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 735533251463053-89-5Yield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-3-chlorobenzoic acid (0.5 g, 2.12 mmol) in toluene (5 mL) were added Et3N (0.3 mL), DPPA (0.69 mL), and t-butanol (7.2 mL). The reaction mixture was heated at 100° C. overnight, cooled, and concentrated. This residue was extracted with ethyl acetate (20 mL). The organic phase was washed with aqueous HCl (5%, 20 mL), saturated NaHCO3, and saturated NaCl, was dried over anhydrous Na2SO4, and was concentrated to give the title compound as a solid (0.4 g, 65%). 1H NMR (400 MHz, CDCl3) δ 8.01 (1H, d, J=8.0 Hz), 7.19-7.12 (1H, m), 7.07-7.05 (2H, m), 1.46 (9H, s).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionThis residue was extracted with ethyl acetate (20 mL)
  4. washThe organic phase was washed with aqueous HCl (5%, 20 mL), saturated NaHCO3, and saturated NaCl
  5. dry with materialwas dried over anhydrous Na2SO4
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-41325430f9764ba5be7915f8329b33a1
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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