(4-Bromophenyl)(4-hydroxyphenyl)methanone → 4-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol

HRID 229276Notes

Reaction equation

HRID 229276 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:27])[CH2:23][C:22](=O)[CH2:21][C:20]([CH3:26])([CH3:25])[O:19]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:22]2[CH2:21][C:20]([CH3:26])([CH3:25])[O:19][C:18]([CH3:27])([CH3:17])[CH2:23]2)[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanoneHCID 118296912,2,6,6-Tetramethyloxan-4-one

Product 1

HCID 686543254-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenolYield 87%

Procedure

The general McMurry procedure, described for 14 was employed using (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (2.10 g, 7.58 mmol), and 2,2,6,6-tetramethyltetrahydro-4H-pyran-4-one (1.40 g, 8.96 g). Standard work-up followed by purification gave 2.64 g (87%) of the title compound 211 as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.37 (s, 1H), 7.49 (d, J=8.7 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.7 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 2.16 (s, 2H), 2.10 (s, 2H), 1.13 (s, 6H), 1.12 (s, 6H). LCMS (ESI): m/z 399 and 401 (M−H)−.

Workup

  1. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-bbc40c31a6cd42b6b74c93e8a58a1234
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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