Ethyl Acetate → HCID 90408707, compound

HRID 516546Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([F:12])=[CH:4][C:3]=1I.C(O[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1)(C)C.[NH4+].[Cl-].C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([F:12])=[CH:4][C:3]=1[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

1,4-difluoro-2-iodo-5-(trifluoromethyl)benzene (500 mg, 1.6 mmol) was dissolved in dry THF (7 mL), cooled to 0° C. and treated in portions with isopropyl magnesium chloride-lithium chloride complex (1.4 mL, 1.3 M, 1.8 mmol) and stirred for 40 min at 5° C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (360 μl, 330 mg, 1.8 mmol) was added and stirring was continued for 1 h. After treating with sat. NH4Cl, the mixture was shaken with ethyl acetate. The organic phase was washed with saturated NaCl, dried (Na2SO4), and evaporated to give the title compound as a light brown oil (500 mg, 100%). The material was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.54 (dd, J=9.9, 4.3 Hz, 1H), 727 (dd, J=8.0, 5.2 Hz, 2H), 1.37 (s, 12H). 19F NMR (376 MHz, CDCl3) δ −62.10, −62.13, −106.85, −106.90, −121.81, −121.87, −121.90.

Workup

additiontreated in portions with isopropyl magnesium chloride-lithium chloride complex (1.4 mL, 1.3 M, 1.8 mmol)
stirringstirring
waitwas continued for 1 h
washThe organic phase was washed with saturated NaCl
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-fef958c5ca9b4ccaa9674b8082c819d8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09113629B2

Reaction notes

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