Sodium Carbonate → HCID 67254694, compound

HRID 536617Notes

Reaction equation

Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:12]#[N:13].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOC(C)=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>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:8])=[CH:3][S:4][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3,4-dibromothiophene (3 g, 12.5 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (2 g, 12.5 mmol), Na2CO3 (2.7 g, 25 mmol), Pd(PPh3)4 (1.4 g, 1.25 mmol) in a mixture of toluene/EtOH/H2O (40 mL, 5:3:2) was stirred at 80° C. under nitrogen overnight. The reaction mixture was diluted with EtOAc (80 mL), and washed with water and brine. The organic phase was dried over Na2SO4, concentrated in vacuo, and purified on silica gel column (PE: EtOAc=30:1) to afford 4-(4-bromothiophen-3-yl)-3-methylbenzonitrile (Scheme III, 13, X1=4-cyano-2-methylphenyl) (2.4 g, yield 68%) as yellow oil. 1H NMR (CD3OD 400 MHz): δ 7.56 (s, 1H), 7.50-7.48 (m, 2H), 7.31 (d, J=3.2 Hz, 1H), 7.22 (d, J=7.6 Hz, 1H), 2.10 (s, 3H).

Workup

washwashed with water and brine
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo
custompurified on silica gel column (PE: EtOAc=30:1)

Sources & evidence

ORD record: ord-3eacde70836241928a06b88412f43348
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859611B2

Reaction notes

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