Sodium Carbonate → t-Butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate

HRID 68602Notes

Reaction equation

Br[C:2]1[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=1)[C:23]#[N:24].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]([C:22]1[CH:25]=[C:26]([C:2]2[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[CH:13][C:3]=2[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:27]=[C:20]([F:19])[CH:21]=1)#[N:24]

Participants

Conditions

Temperature: 80 °C

Procedure

To solution of tert-butyl 2-(2-bromo-4-formylphenoxy)acetate (1) (120 g, 0.38 mol) in dioxane/H2O (4:1, 700 mL) was added 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (20) (158 g in 60% purity, 0.38 mol), Na2CO3 (81 g, 0.76 mol) and Pd(PPh3)4 (22 g, 19 mmol) under N2. The mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the mixture was concentrated in vacuo and purified by column chromatography (PE:EA=10:1 v/v) to give 90 g of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate (21) (90 g, 67%).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo
custompurified by column chromatography (PE:EA=10:1 v/v)

Sources & evidence

ORD record: ord-2b5526d4c9734bb884f049027cce490b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822467B2

Reaction notes

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