2-Bromotoluene → HCID 68964104, compound

HRID 902345Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].C(=O)([O-])[O-].[Na+].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=1B(O)O>COCCOC.O.[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>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8]

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of 2-bromotoluene (13.8 g, 80.6 mmol) and sodium carbonate (9.0 g, 84.9 mmol) in DME-water (5:1, 250 mL) was added 2-chloro-6-methoxybenzene boronic acid (5.0 g, 26.8 mmol) at 82° C., followed by tetrakis(triphenylphosphine)-palladium (0) (1.5 g, 1.4 mmol). The reaction mixture was heated at 82° C. overnight and cooled to room temperature. The resulting mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride, dried (Na2SO4) and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 5% ethyl acetate in hexanes provided 3.9 g (62%) of 2-chloro-6-methoxy-2′-methylbiphenyl as a colorless oil.

Workup

temperaturecooled to room temperature
extractionThe resulting mixture was extracted with ethyl acetate
washwashed with water and saturated sodium chloride
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customPurification by ISCO

Sources & evidence

ORD record: ord-a813aae172f844b0a4fbc9470c7ce1a7
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365095B2

Reaction notes

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