Ethyl Bromide → HCID 25064370, compound

HRID 909403Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])[N:8]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:5]=2[CH:4]=1.[Br:32]CC.[Br-].[Na+]>O.CC(O)C.CN1CCCC1=O>[Br:32][CH2:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])[N:8]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 57.5 °C

Procedure

10.0 g of 6-(chloromethyl)-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one, 35 mL of bromoethane and 2.42 g of sodium bromide were added to 80 mL of N-methyl-2-pyrrolidone, and this was stirred for 1.5 hours at 55-60° C. After cooling the reaction mixture, 20 mL of 2-propanol and 50 mL of water were added dropwise and solids were filtered to obtain a white solid. The obtained white solid, 35 mL of bromoethane and 2.42 g of sodium bromide were added to 80 mL of N-methyl-2-pyrrolidone, and this was stirred for 1 hour at 55-60° C. After cooling the reaction mixture, 20 mL of 2-propanol and 50 mL of water were added dropwise and solids were filtered to obtain 9.04 g of 6-(bromomethyl)-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one in the form of a white solid.

Workup

additionwere added dropwise
filtrationsolids were filtered
customto obtain a white solid
stirringthis was stirred for 1 hour at 55-60° C
additionwere added dropwise
filtrationsolids were filtered

Sources & evidence

ORD record: ord-1736c27fffa84244bea1bff80a2805c5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017789B2

Reaction notes

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