2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 84266

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([F:9])[C:3]=1[F:10].C(O[B:15]1[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]1)(C)C>O1CCCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([B:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]2)=[C:3]([F:10])[C:4]=1[F:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-bromo-4-chloro-2,3-difluorobenzene (720 mg, 3.17 mmol) in tetrahydrofuran (10 mL) was added i-propylmagesiumchloride (1.90 mL, 3.80 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. Then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (0.98 mL, 4.75 mmol) in tetrahydrofuran (5.0 mL) was added. The reaction mixture was allowed to warm up to room temperature and stirred at RT for 1 h. The mixture was used directly in the next step.

Workup

temperatureto warm up to room temperature
stirringstirred at RT for 1 h

Sources & evidence

ORD record: ord-551db3ac9e5b473cb2006f123badb186
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846933B2

Linked notes

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