Aniline → Tribromophenol Triphenylphosphite Aniline Propylene Oxide Triethylamine

HRID 1076844Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Br:9])[C:3]=1[Br:10].[Al].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]1([O:25][P:26]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:41]1[O:44][CH:42]1[CH3:43]>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Br:9])[C:3]=1[Br:10].[C:35]1([O:34][P:26]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:41]1[O:44][CH:42]1[CH3:43].[CH2:19]([N:12]([CH2:7][CH3:2])[CH2:13][CH3:18])[CH3:20]

Participants

Conditions

Temperature: 130 °C

Procedure

A 1-liter flask, standardly equipped, was charged with 331 grams of tribromophenol containing between 700 and 800 ppm of aluminum and ferric compounds, 46.5 grams of aniline and 180 grams of triphenylphosphite. After heating the mixture to 130°C., 145 ml. of propylene oxide was added at a temperature up to 155°C. After cooling, 5 grams of triethylamine was added followed by the addition of 80 ml. of propylene oxide at approximately 80°C. The mixture was then stripped of volatile materials at 80°C./1 mm. Hg to remove volatiles. There remained as residue 632.8 grams of oxypropylated product having a hydroxyl number of 170, an acid number of 1.9 and the product contained 38.5 percent bromine and 2.8 percent phosphorus.

Workup

customA 1-liter flask, standardly equipped
temperatureAfter cooling
additionfollowed by the addition of 80 ml
customat approximately 80°C
customwas then stripped of volatile materials at 80°C.
customto remove volatiles

Sources & evidence

ORD record: ord-04a8b995433643c7865391ea4a5fd188
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03957922

Reaction notes

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