Sodium Carbonate → 2-(2-Fluoro-4-methylphenyl)benzaldehyde

HRID 1422144Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)=[O:11].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C(CCO)=CC=CC=1>C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:10]=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2 g of 4-bromo-3-fluorotoluene, 1.75 g of 2-formylbenzeneboronic acid, 0.36 g of tetrakis(triphenylphosphine)-palladium (0) and 11.6 ml of 2N aqueous sodium carbonate, in 50 ml of a 9:1 mixture of toluene-ethanol was heated to 100° C. for 3 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica gel eluting with ethyl acetate-heptane (1:3) to give 1.62 g of 2-(2-fluoro-4-methylphenyl)benzaldehyde as an oil, GC-M.S. (E.I.) (M/Z): 214 [M+ ].

Workup

temperatureThe mixture was cooled to room temperature
washwashed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia
dry with materialThe organic layer was dried over sodium sulfate
customevaporated to dryness under reduced pressure
customThe resulting oil was purified by chromatography on silica gel eluting with ethyl acetate-heptane (1:3)

Sources & evidence

ORD record: ord-700329f16c5c438e8df54f40e3f798aa
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080773

Reaction notes

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