Water → 4-(4-Trifluoromethylphenyl)thiophene-2-carbaldehyde

HRID 9639

Reaction equation

Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.[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:10]([F:21])([F:20])[C:11]1[CH:12]=[CH:13][C:14]([C:6]2[CH:2]=[C:3]([CH:7]=[O:8])[S:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-bromothiophene-2-carboxaldehyde (2.0 g) and 3-trifluoromethylbenzene boronic acid (2.19 g) in ethylene glycol dimethyl ether (100 ml) was added sodium carbonate (2.9 g), tetrakis(triphenylphosphine) palladium (0) (0.12 g) and water (50 ml). The mixture was heated to 90° C. under nitrogen. After 18 hours the reaction was allowed to cool and was concentrated. The residue was partitioned between water and ethyl acetate; the organic solution was taken and was washed with brine and then dried (MgSO4) and concentrated. The crude material was purified by SPE (Si); the product eluted with neat chloroform to furnish the title compound as a yellow solid.

Workup

temperatureto cool
concentrationwas concentrated
customThe residue was partitioned between water and ethyl acetate
washwas washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude material was purified by SPE (Si)
washthe product eluted with neat chloroform

Sources & evidence

ORD record: ord-ffa3f6e62ec945dc861cc1427e46b8f0
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091237B2

Linked notes

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