2-Bromophenol → 2-(1-Methyl-1H-pyrrol-2-yl)phenol

HRID 2204121Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1B1OC(C)(C)C(C)(C)O1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.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>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]

Participants

Conditions

Temperature: 80 °C

Procedure

1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole (5.0 g, 24 mmol), tetrakis(triphenylphosphine)palladium (0) (1.4 g, 1.2 mmol), 2-bromophenol (4.2 g, 24 mmol), and potassium carbonate (24 mL of 2.0 M, 48 mmol) were combined in 1,2-dichloroethane (291 mL). The mixture was heated at 80° C. for 16 h. The mixture was cooled to 25° C. before it was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, and concentrated. Column chromatography (0-100% ethyl acetate/hexanes) on the residue gave 2-(1-methylpyrrol-2-yl)phenol (1.4 g, 34%). ESI-MS m/z calc. 173.2, found 174.2 (M+1)+; Retention time: 1.76 minutes (3 min run).

Workup

temperatureThe mixture was cooled to 25° C. before it
customwas partitioned between ethyl acetate and water
customThe layers were separated
washthe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-54e2e736a40c4842b35ad8c3e9109cae
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365588B2

Reaction notes

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