Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 68551028, compound

HRID 1868047Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])=[O:12].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([F:30])([F:29])[F:28].CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH:14]1[CH2:19][CH2:18][N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH2:16][CH2:15]1)(=[O:12])=[O:13]

Participants

Conditions

Temperature: 90 °C

Procedure

A 5 mL microwave reaction vial was charged with 4-(2-naphthylsulfonyl)piperidine (82 mg, 0.30 mmol), 2-bromobenzotrifluoride (67 mg, 0.30 mmol), NaOt-Bu (40 mg, 0.42 mmol), Pd2(dba)3 (26 mg, 0.025 mmol), racemic BINAP (31 mg, 0.05 mmol), and dioxane (1.5 mL). The mixture was degassed with N2, capped, and heated in a 90° C. oil bath for 16 h. The mixture was diluted with CH2Cl2 (10 mL) and filtered through a plug of SiO2. The organic phase was concentrated and purified by SiO2 chromatography (15 to 30% EtOAc-hex) to afford the title compound (63 mg), a yellow oil, in 50% yield.

Workup

customA 5 mL microwave reaction
customThe mixture was degassed with N2
customcapped
additionThe mixture was diluted with CH2Cl2 (10 mL)
filtrationfiltered through a plug of SiO2
concentrationThe organic phase was concentrated
custompurified by SiO2 chromatography (15 to 30% EtOAc-hex)

Sources & evidence

ORD record: ord-fae67ff6530d415798b9249e1e2f10d6
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632838B2

Reaction notes

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