Hydrogen Bromide → Bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide

HRID 2180206Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:27])([C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)[C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[CH:5][CH:4]=1.Br.[K+].[Br-].S([O-])([O-])=O.[Na+].[Na+].CBr>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:27])([C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[CH:5][CH:4]=1

Participants

Reactant 5

HCID 260Hydrogen Bromide

HCID 6323Methyl Bromide

HCID 24437Sodium Sulfite

HCID 253877Potassium Bromide

HCID 22290123Bis(4-methoxyphenyl)-2,4,5-trimethylphenylphosphine oxide

Product 1

HCID 22290104Bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxideYield 68.9%

Conditions

Temperature: 118 °C

Procedure

A reaction flask containing the bis(4-methoxyphenyl)-2,4,5-trimethylphenylphosphine oxide mixture (443.7 g) was charged with 48% aq. HBr (934 mL) and KBr (59.5 g). The flask was fitted with a sodium sulfite scrubber for containment of methyl bromide. The reaction mixture was heated to reflux (118° C.) and maintained at reflux until complete based on HPLC analysis. The molten product was worked up to give 283.3 g of bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide mixture as a cream solid (68.9% yield). The ratio of products in the mixture based on 31P NMR was 39% tris(4-hydroxyphenyl)phosphine oxide, 49% bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide, 11% di-2,4,5-trimethylphenyl-4-hydroxyphenyl-phosphine oxide, and 1% tris(2,4,5-trimethylphenyl)phosphine oxide.

Workup

temperatureThe reaction mixture was heated
temperaturemaintained
temperatureat reflux

Sources & evidence

ORD record: ord-59d50adcd7a64ced8cfd8ccef7f9b0a9
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887950B2

Reaction notes

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