Hydrochloric Acid → 1222509-12-7

HRID 60568Notes

Reaction equation

HRID 60568 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[CH:11][C:6]2[CH2:7][O:8][B:9]([OH:10])[C:5]=2[CH:4]=1.C(N(CC)CC)C.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[C:23]([C:30]([F:33])([F:32])[F:31])[CH:22]=1.Cl>ClCCl>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:2][C:3]2[CH:12]=[CH:11][C:6]3[CH2:7][O:8][B:9]([OH:10])[C:5]=3[CH:4]=2)=[O:26])=[C:23]([C:30]([F:31])([F:32])[F:33])[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 441187306-Amino-2,1-benzoxaborol-1(3H)-ol--hydrogen chloride (1/1)

Product 1

HCID 461821301222509-12-7Yield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 ml round bottom flask was charged with a mixture of 6-amino-1-hydroxy-2,1-benzoxaborolane hydrochloride (5 g, 26.9 mmol, 1 eq), triethylamine (11.2 ml, 80.7 mmol, 3 eq) and dichloromethane (200 ml). 4-Fluoro-2-(trifluoromethyl)benzoyl chloride (4.3 ml, 28.2 mmol, 1.05 eq) was then added, and the reaction mixture was allowed to stir at room temperature overnight. 1M HCl (100 ml) was added to the mixture and the reaction was stirred for an additional hour. The resulting precipitate was then collected, and the off-white powder was dried under vacuum. LCMS (m/e) 340 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.96 (s, 2 H) 7.39 (d, J=8.4 Hz, 1 H) 7.61-7.73 (m, 2 H) 7.75-7.87 (m, 2 H) 8.13 (dd, J=1.8, 0.4 Hz, 1 H) 9.25 (s, 1 H) 10.59 (s, 1 H) Amount Obtained: 5.2 g, 57% yield.

Workup

  1. stirringthe reaction was stirred for an additional hour
  2. customThe resulting precipitate was then collected
  3. customthe off-white powder was dried under vacuum
  4. custom1H NMR (400 MHz, DMSO-d6) δ ppm 4.96 (s, 2 H) 7.39 (d, J=8.4 Hz, 1 H) 7.61-7.73 (m, 2 H) 7.75-7.87 (m, 2 H) 8.13 (dd, J=1.8, 0.4 Hz, 1 H) 9.25 (s, 1 H) 10.59 (s, 1 H) Amount Obtained

Sources & evidence

ORD record
ord-b9659db921ab4a9ea81a580121637038
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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