Formic Acid → Tert-butyl N-[(Benzenesulfonyl)(2-bromo-4-cyanophenyl)methyl]carbamate

HRID 59651

Reaction equation

HRID 59651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[Na+].[C:13]1([S:19]([O-:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([NH:26][C:27](=[O:29])[O-:28])(C)(C)C.[CH:30](O)=O.[CH2:33]1[CH2:37]OC[CH2:34]1>O>[C:33]([O:28][C:27](=[O:29])[NH:26][CH:10]([S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20])[C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Br:1])([CH3:34])([CH3:37])[CH3:30]

Participants

7

Reactant 5

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 2723840Benzenesulfinic acid, sodium saltHCID 205105183-Bromo-4-formylbenzonitrileHCID 21252905Tert-butylcarbamate

Product 1

HCID 118691238Tert-butyl N-[(Benzenesulfonyl)(2-bromo-4-cyanophenyl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Bromo-4-formyl-benzonitrile (20.5 g, 97.7 mmol), benzenesulfinic acid sodium salt (16.03 g, 97.6 mmol) and tert-butylcarbamate (11.4 g, 97.7 mmol) are suspended in water (312 mL) and THF (78 mL). Formic acid (28.8 g, 625 mmol) is added and the solution is stirred at room temperature for 6 days. Water (300 mL) is added and the precipitate is filtered off, washed with water and dried. The crude product is further purified by precipitation from tert-butylmethylether. Yield: 26.8 g; ESI mass spectrum: [M+Na]+=473 (bromine isotope pattern).

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with water
  3. customdried
  4. customThe crude product is further purified by precipitation from tert-butylmethylether

Sources & evidence

ORD record
ord-3e802816fb3946918173d636cb788fa2
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Linked notes

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