Chloroacetyl chloride → 6238-97-7

HRID 417932Notes

Reaction equation

HRID 417932 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].C(N(CC)CC)C.Cl[CH2:19][C:20](Cl)=[O:21].[H-].[Na+]>C1COCC1>[Br:8][C:6]1[C:5]([CH3:9])=[CH:4][C:3]2[O:10][CH2:19][C:20](=[O:21])[NH:1][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 202516862-Amino-4-bromo-5-methylphenol

Product 1

HCID 666487486238-97-7Yield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared following the procedure for Intermediate 6 using 2-amino-4-bromo-5-methylphenol (4.73 g, 23.4 mmol), triethylamine (3.6 mL, 25.8 mmol) and chloroacetyl chloride (1.8 mL, 23.4 mmol) in THF (120 mL) followed by sodium hydride (1.9 g of a 60% suspension in oil, 49.2 mmol) to give the title compound (4.12 g, 73%) as a beige solid. δH (DMSO-d6) 2.23 (3H, s), 4.57 (2H, s), 6.97 (1H, s), 7.04 (1H, s), 10.72 (1H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0e12a6f6794546f89b30e7f036514148
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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