[ CAS No. 1035235-27-8 ]

Name: tert-Butyl 4-bromoisoindoline-2-carboxylate
Brand: Ambeed
SKU: A152606
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Quality Control of [ 1035235-27-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1035235-27-8 ]

CAS No. :	1035235-27-8	MDL No. :	MFCD10700130
Formula :	C₁₃H₁₆BrNO₂	Boiling Point :	363.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	298.18	Pubchem ID :	49853504
Synonyms :

Computed Properties of [ 1035235-27-8 ]

TPSA :Topological Polar Surface Area	29.5	H-Bond Acceptor Count :	2
XLogP3 :	2.9	H-Bond Donor Count :	0
SP3 :	0.46	Rotatable Bond Count :	2

Safety of [ 1035235-27-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1035235-27-8 ]

Upstream synthesis route of [ 1035235-27-8 ]
Downstream synthetic route of [ 1035235-27-8 ]

[ 1035235-27-8 ] Synthesis Path-Upstream 1~3

1
[ 923590-95-8 ]
[ 24424-99-5 ]
[ 1035235-27-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In tetrahydrofuran at 10 - 20℃; for 12 h;	Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10°C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20°C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 χ 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75percent). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) δ ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).

Reference： [1] Patent: WO2017/158388, 2017, A1, . Location in patent: Page/Page column 55; 214
[2] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7576 - 7582

2
[ 24424-99-5 ]
[ 1035235-27-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 18 h;	A solution of 4-bromoisoindoline hydrochloride (1.40 g, 5.97 mmol) in DMF (30 mL) was treated with triethylamine (2.50 mL, 17.9 mmol) and di-tert-butyl dicarbonate (2.08 mL, 8.95 mmol), and the mixture was stirred at room temperature for 18 h. Themixture was diluted with EtOAc (65 mL) and washed three times with saturated aqueousNaHCO3. The organic phase was dried and concentrated. The residue was subjected tocolumn chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-3 0percent), to provide tert-butyl 4-bromoisoindoline-2-carboxylate as a white solid (1.70 g,91percent yield).

Reference： [1] Patent: WO2016/65236, 2016, A1, . Location in patent: Page/Page column 118

3
[ 127168-81-4 ]
[ 24424-99-5 ]
[ 1035235-27-8 ]

Reference： [1] Patent: US2008/171754, 2008, A1, . Location in patent: Page/Page column 104

[ 1035235-27-8 ] Synthesis Path-Downstream 1~1

1
[ 127168-81-4 ]
[ 24424-99-5 ]
[ 1035235-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; water; at 20℃;	Step 4: tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate To a solution of 4-bromoisoindolin-1-one (4 mmol) in THF (8 mL) was added borane-dimethyl sulfide complex (2M in THF, 14 mL) at 0 C. The reaction mixture was allowed to stir at reflux overnight and was then cooled to 0 C. The reaction mixture was quenched by the slow addition of MeOH (2 mL) and then 3N HCl. The reaction mixture was allowed to stir at reflux for 3 hr and then concentrated. Water was added to the residue and the pH of the solution was adjusted to >9 with 4N NaOH. The solution was extracted with diethyl ether. The organic solutions from this basic extraction were combined, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindoline, which was dissolved in THF (5 mL). To this solution was added potassium carbonate (4 mmol) in water (0.5 mL), and BOC2O (2 mmol). The reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.8 mmol, 20%).

Reference： [1]Patent: US2008/171754,2008,A1 .Location in patent: Page/Page column 104

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1035235-27-8 ]

Quality Control of [ 1035235-27-8 ]

Related Doc. of [ 1035235-27-8 ]

Product Details of [ 1035235-27-8 ]

Computed Properties of [ 1035235-27-8 ]

Safety of [ 1035235-27-8 ]

Application In Synthesis of [ 1035235-27-8 ]

[ 1035235-27-8 ] Synthesis Path-Upstream 1~3

[ 1035235-27-8 ] Synthesis Path-Downstream 1~1

Related Functional Groups of [ 1035235-27-8 ]

Bromides

Amides

Related Parent Nucleus of [ 1035235-27-8 ]

Indolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1035235-27-8 ]

Related Parent Nucleus of
[ 1035235-27-8 ]