* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With dmap; copper (I) acetate In toluene at 120℃; for 8 h; Inert atmosphere
Under argon protection,To the drying reactor was added 1 L of toluene,Followed by the addition of N, N-dimethylaniline (121 g, 1 mol)4-dimethylaminopyridine (122 g, 1 mol),Cuprous acetate (1.2 g, 0.01 mmol)And di-tert-butylphosphonium chloride (181 g, 1 mol)And then heated to 120 C for 8 hours.After completion of the reaction, 1 L of water was added to the quenching reaction,Then extracted,The organic layer was dried over anhydrous magnesium sulfate,filter,After distillation under reduced pressure to give a yellow solid,This was lyophilized in 1 L of n-hexane to recrystallize to give a white solid [4- (N, N-dimethylamino) phenyl] di-tert-butylphosphine 254 g,Yield 96percent.
Reference：
[1] Patent: CN106349286, 2017, A, . Location in patent: Paragraph 0009; 0010
2
[ 13716-10-4 ]
[ 108949-55-9 ]
[ 932710-63-9 ]
Yield
Reaction Conditions
Operation in experiment
85%
Stage #1: at -30℃; for 0.166667 h; Inert atmosphere Stage #2: With ammonium chloride In water at -30℃; for 0.5 h;
The reaction system is cooled to -30 ° C, under the protection of nitrogen flow,Adding catalyst to remove water by vacuum dryingAfter the powder was 10.2 g, the reaction was stirred for 10 min.Further, 930 g of di-tert-butylphosphonium chloride was added dropwise.The dropping process controls the reaction temperature below -30 ° C, and the dropwise addition is completed, and the temperature is raised to 50 ° C for 3 hours to obtain di-tert-butyl-4-dimethylaminophenylphosphine. The reaction system was again cooled to -30 ° C, and 1.5 L of a saturated aqueous solution of ammonium chloride was added dropwise with stirring.After stirring for 0.5 h, the mixture was allowed to stand for stratification under the protection of a nitrogen stream.The liquid is separated, and the upper organic phase is concentrated and concentrated to obtain a yellow viscous material for high vacuum distillation under reduced pressure.The degree of vacuum is 0.3-0.5 mmHg, and the fraction of 120 ° C - 140 ° C is collected, and after cooling, it is an off-white solid.That is, the ligand di-tert-butyl-4-dimethylaminophenylphosphine has a yield of 1145-1160 g, a purity of not less than 97percent, and a yield of 81.5percent to 85.0percent.
Reference：
[1] Patent: CN108659054, 2018, A, . Location in patent: Paragraph 0057; 0059; 0060
3
[ 13716-10-4 ]
[ 7353-91-5 ]
[ 932710-63-9 ]
Yield
Reaction Conditions
Operation in experiment
85%
Stage #1: at -60℃; for 0.133333 h; Inert atmosphere Stage #2: With ammonium chloride In water at -60℃; for 0.5 h;
The reaction system is cooled to -60 ° C under the protection of nitrogen flow.Adding catalyst to the vacuum drying to remove water, copper bromideAfter the powder was 14.8 g, the reaction was stirred for 8 min, and 930 g of di-tert-butylphosphonium chloride was added dropwise.The dropping process controls the reaction temperature below -60 ° C, and the dropwise addition is completed, and the temperature is raised to 55 ° C for 4 hours to obtain di-tert-butyl-4-dimethylaminophenylphosphine. The reaction system was again cooled to below -60 ° C, and 1.5 L of a saturated aqueous solution of ammonium chloride was added dropwise with stirring, and the mixture was stirred for 0.5 h.After standing and layering,The liquid is separated under the protection of a nitrogen stream, and the upper organic phase is concentrated and concentrated to obtain a yellow viscous material for high vacuum distillation under reduced pressure.The degree of vacuum is 0.3-0.5 mmHg, and the fraction of 120 ° C - 140 ° C is collected, and after cooling, it is an off-white solid.It is a ligand of di-tert-butyl-4-dimethylaminophenylphosphine, and the yield is 1145-1160 g, the purity is not less than 97percent, and the yield is 81.5percent to 85.0percent.
Reference：
[1] Patent: CN108659054, 2018, A, . Location in patent: Paragraph 0062; 0064; 0065
4
[ 819-19-2 ]
[ 586-77-6 ]
[ 932710-63-9 ]
Yield
Reaction Conditions
Operation in experiment
49.2 g
Stage #1: With n-butyllithium In hexane; toluene at 50℃; for 12 h; Inert atmosphere Stage #2: at 5℃; for 12 h; Inert atmosphere
The reaction flask was replaced with a nitrogen atmosphere, and 32 g of di-tert-butylphosphine and 200 mL of toluene were added to 1 L of the reaction flask,Start the magnetic stirrer, add 0.1M 2.5M n-butyllithium at -10 ° C, drip to 50 ° C for 12 hours, drop the temperature of the reaction solution to -10 ° C,A solution of 40 g of N, N-dimethyl-p-bromoaniline in toluene was added dropwise to the reaction at 50 ° C for 12 hours, after which the reaction solution was lowered to room temperature,10 mL of triethylamine aqueous solution was added dropwise under ice-cooling, and the upper organic phase was depiltrated under nitrogen protection,Distillation under reduced pressure, collecting 120 ° C (15 mm Hg) di-tert-butyl-4-dimethylaminophenylphosphine 49.2 g
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